Pyridine derivatives, process for preparing the same and their use for controlling animal pests and harmful fungi

ABSTRACT

Pyridine derivatives of the formula I                    
     and their salts, their preparation, and their use for controlling animal pests and harmful fungi.

The present invention relates to pyridine derivatives of the formula I

where the index and the substituents have the following meanings:

X is cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and C₃-C₆-cycloalkyl;

n is 0, 1, 2 or 3, it being possible for the substituents X to be different when n is greater than 1;

Y is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C₁-C₄-alkyl group;

R is C(CO₂CH₃)═CHCH₃, C(CO₂CH₃)═CHOCH₃, C(CO₂CH₃)═NOCH₃, C (CONH₂)═NOCH₃ or C (CONHCH₃)═NOCH₃;

R¹ is hydrogen, hydroxyl, cyano, halogen,

C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,

aryl, aryl-C₁-C₄-alkyl, aryloxy-C₁-C₄-alkyl and aryl-C₁-C₄-alkoxy, it being possible for the aromatic rings to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, and C (CH₃)═N—A¹—Ra;

R^(a) is C₁-C₆-alkyl,

A¹ is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C₁-C₄-alkyl group;

R² is hydrogen, cyano,

unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and hetaryl;

unsubstituted or substituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, heterocyclyloxy, aryloxy and hetaryloxy;

unsubstituted or substituted arylthio and hetarylthio;

—Q—C(R³)═N—Y¹—R⁴ or —Q—O—N═CR⁵R⁶ where

Q is a direct bond, CH₂, CH(CH₃), CH(CH₂CH₃) or 1,1-cyclopropyl;

Y¹ is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C₁-C₄-alkyl group;

R³ is one of the groups mentioned for R¹, or unsubstituted or substituted cycloalkoxy, heterocyclyloxy, aryloxy, hetaryloxy, arylthio and hetarylthio;

R⁴ is unsubstituted or substituted C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₁₀-alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl, C₂-C₁₀-alkynylcarbonyl or C₁-C₁₀-alkylsulfonyl; unsubstituted or substituted aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl;

R⁵, R⁶ are methyl, ethyl, phenyl and benzyl, it being possible for the aromatic rings to have attached to them one to three of the following substituents: cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;

R¹ and R² together with the carbon atom to which they are bonded are a four- to eight-membered ring which, in addition to carbon atoms, can contain one or two oxygen and/or sulfur atoms and/or NH and/or N(C₁-C₄-alkyl) groups and whose carbon atoms can have attached to them one of the following substituents: halogen, C₁-C₆-alkyl or C₁-C₄-alkoxyimino;

R¹ and R² not being bonded simultaneously to the carbon atom via hetero atoms;

and the salts thereof.

Moreover, the invention relates to processes for the preparation of these compounds, to compositions comprising them, and to their use for controlling animal pests and harmful fungi.

Compounds of the type I where Y is oxygen and R² is unsubstituted or substituted aryl or hetaryl are described in the literature in general form as fungicides (WO-A 95/06,033). However, only compounds which have attached to them an unsubstituted or substituted aryl group which is bonded to the pyridyl radical via oxygen, sulfur, oxymethylene or CH₂—ON═C(CH₃)— are disclosed in this publication.

It was an object of the present invention to provide compounds with an improved activity and a broadened spectrum of action.

We have found that this object is achieved by the compounds I defined at the outset. Furthermore, we have found processes for the preparation of these compounds, compositions comprising them, and their use for controlling animal pests and harmful fungi.

The compounds I can be prepared by various routes, it generally being irrelevant whether the group —Y—N═CR¹R² or the radical R is first synthesized.

1. In the preparation of the compounds I where R is C(CO₂CH₃)═CHCH₃, C(CO₂CH₃)═CHOCH₃ or C(CO₂CH₃)═NOCH₃, a procedure is followed, for example, in which a pyridinecarboxylic acid of the formula IIa is first converted in a manner known per se into the acid chloride IIb and subsequently into the acid cyanide IIc; IIc is reacted via a Pinner reaction to give the corresponding α-keto ester IIIa; IIIa is subsequently reacted with an oxime of the formula IV in the presence of a base to give the corresponding α-keto ester IIIb; and IIIb is subsequently converted in a manner known per se either

a) with a Wittig or Wittig-Horner reagent of the formula Va into the corresponding compound Ia [R=C(CO₂CH₃)═CHOCH₃], or

b) with a Wittig or Wittig-Horner reagent of the formula Vb into the corresponding compound Ib [R=C(CO₂CH₃)═CHCH₃], or

c) with O-methylhydroxylamine or a salt thereof (Vc) into the corresponding compound Ic [R=C(CO₂CH₃)═NOCH₃].

L¹ in formula IIa is a nucleophilically exchangeable leaving group such as [lacuna]

R# in formula IIa is hydrogen or a C₁-C₄-alkyl group, in particular hydrogen.

P* in formulae Va and Vb is a phosphonate or a phosphonium halide radical which is suitable for a Wittig or Wittig-Horner reaction, in particular PO(OCH₃)₂, PO(OCH₂CH₃)₂ and [(C₆H₅)₃P⁺Cl⁻].

Z⁻ in formula Vc is the anion of an inorganic acid, especially a halide anion, in particular chloride.

1A. The reaction of the pyridinecarboxylic acid IIa to give the acid chloride IIb is carried out in a manner known per se [Houben-Weyl, Supplementary Volume 5, p.59 et seq., 225 et seq. and 664 et seq.; J.Heterocycl.Chem, 30, (1993), 771] by means of customary chlorinating agents at from 0° C. to 150° C., preferably 10° C. to 100° C., in the presence or absence of an inert organic solvent.

Suitable chlorinating agents are all reagents customary for this purpose, in particular SOCl₂, (COCl)₂, PCl₃, AlCl₃ and PCl₅. In general, the chlorinating agents are used in an excess or, if appropriate, as the solvent.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, nitrites such as acetonitrile and propionitrile, especially preferably halogenated hydrocarbons or mixtures of these.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ the chlorinating agent in an excess based on IIa.

The starting materials required for the preparation of the compounds I which are not already known from the literature [WO-A 95/06,033; J.Heterocycl.Chem. 30, (1993), 717; DE Appl. No. 19 540 989.2; DE Appl. No. 19 548 370.7] can be prepared in accordance with the literature cited.

1B. The reaction of the acid chloride IIb to give the cyanide IIc is carried out in a manner known per se [DE Appl. No. 19 603 990.8] at from 0° C. to 150° C., preferably 10° C. to 100° C., using an inorganic cyanide in an inert organic solvent, if appropriate as a mixture with water, in the presence of a customary phase-transfer catalyst (eg. tetraalkylammonium halides such as tetrabutylammonium chloride or tetrabutylammonium bromide).

Suitable inorganic cyanides are cyanides of metals of the first main group or of the sub-groups of the Periodic Table, for example lithium, sodium, potassium, copper and silver, in particular copper and sodium, and inorganic cyanides such as trimethylsilyl cyanide.

Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, nitrites such as acetonitrile and propionitrile, especially preferably methylene chloride and acetonitrile. Mixtures of these may also be used.

When using organic cyanides such as trimethylsilyl cyanide, it may be advantageous to carry out the reaction in the presence of an acidic catalyst. Acidic catalysts which are used are Lewis acids such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zink(II) chloride, in particular tin(IV) chloride.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ the cyanide in an excess based on IIb.

1C. The reaction of the cyanide IIc to give the α-keto ester IIIa is carried out in a manner known per se via a Pinner reaction [DE Appl. No. 19 603 990.8] at from 0° C. to 150° C., preferably 10° C. to 100° C., in the presence of an acid in methanol as the solvent.

Acids which are used are inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid. In general, the acids are used in equimolar amounts or in an excess.

The reaction is usually carried out in such a way that the cyanide IIc is first hydrolyzed with aqueous acids (eg. hydrochloric acid) at from 10° C. to 100° C. and the product is subsequently esterified by reaction with methanol, in the presence or absence of a reaction auxiliary (eg. sulfuric acid) and in the presence or absence of a diluent (eg. toluene) at from 10° C. to 150° C. by methods similar to known processes [EP-A 493 711].

1D. The reaction of the α-keto ester IIIa with the oxime of the formula IV is carried out in a manner known per se at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence of a base.

Suitable solvents are alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably dimethylformamide, dimethylacetamide, dimethyl sulfoxide and tert-butanol. Mixtures of these may also be used.

Bases which are generally suitable are inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, and also alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Potassium tert-butoxide, potassium carbonate and sodium methoxide are especially preferred.

In general, the bases are used in equimolar amounts, in an excess or, if appropriate, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ IV in an excess based on IIIa.

1E. The reaction of the α-keto ester IIIb to give the compound Ia is carried out in a manner known per se [EP-A 513 580; tetrahedron 3727 (1988); GB-A 2,172,595; DE Appl. No. 19 603 990.8] via a Wittig or Wittig-Horner reaction at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence of a base.

Suitable solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably dimethylformamide, dimethylacetamide and tetrahydrofuran. Mixtures of these may also be used.

Bases which are suitable are, generally, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride, and alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium. Sodium methoxide and potassium tert-butoxide are especially preferred.

In general, the bases are used in equimolar amounts, in an excess or, if appropriate, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ Va in an excess based on IIIb.

1F. The reaction of the α-keto ester IIIb to give the compound Ib is carried out a manner known per se (cf. the references cited under 1E.) via a Wittig or Wittig-Horner reaction at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence of a base.

Suitable solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably dimethyl sulfoxide, dimethylformamide, dimethylacetamide and tetrahydrofuran. Mixtures of these can also be used.

Bases which are suitable are, generally, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesuim halides such as methylmagnesium chloride, and alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium. Sodium methoxide and potassium tert-butoxide are especially preferred.

In general, the bases are used in equimolar amounts, in an excess or, if appropriate, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ Vb in an excess based on IIb.

1G. The reaction of the α-keto ester IIIb to give the compound Ic is carried out in a manner known per se (EP-A 493 711) at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence of a base using O-methylhydroxylamine or a salt thereof (Vc).

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably methanol. Mixtures of these may also be used.

Bases which are generally suitable are inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Tertiary amines are especially preferred.

The bases are generally employed in catalytic amounts, but they can also be used in equimolar amounts, in an excess or, if appropriate, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ Vc in an excess based on IIIb.

2. In a further process, the compounds Ia, Ib and Ic are obtained, for example, by converting a pyridine derivative of the formula VI with a compound VII in a manner known per se in the presence of a catalyst into the corresponding pyridine derivative of the formula VIII and subsequently reacting VIII with an oxime of the formula IV in the presence of a base to give Ia, Ib or Ic. The pyridine derivatives VIII are also obtained in a similar manner by reacting a halogenated pyridine of the formula VIa with an organometallic compound VIIa.

L¹ in formulae VI, VIa and VIII is a nucleophilically exchangeable leaving group, such as aliphatic and aromatic sulfonates and halogen atoms, in particular fluorine and chlorine.

M in formulae VI and VIIa is an organometallic radical, eg. tributyltin(IV), trimethyltin(IV), zink(II) chloride (ZnCl) or boron(II) hydroxide [B(OH)₂], in particular tributyltin(IV) and boron(II) hydroxide [B(OH)₂]. With a view to the high toxicity of trimethyltin(IV), this substance is preferred only under certain conditions.

T in formulae VII, VIIa, VIII and Ia, Ib or Ic is CH, CHO or NO.

Hal in formulae VIa and VII is a halogen atom, in particular bromine or iodine.

2A. The reaction of the compound VI, or VIa, with the carbonyl derivative VII, or VIIa, is carried out in a manner known per se at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence or absence of a cocatalyst such as CuI. In the event that the reaction is carried out with the compound VI or VIIa where M is B(OH)₂, the reaction is carried out in the presence of at least equimolar amounts of a base.

Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, and also dimethylformamide and dimethylacetamide, especially preferably N-methylpyrrolidone. Mixtures of the abovementioned solvents can also be used.

Bases which are suitable for coupling compounds where M is B(OH)₂ are, generally, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, and also alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Sodium carbonate, sodium hydrogen carbonate and lithium hydroxide are especially preferred.

In general, the bases are used in equimolar amounts, in an excess or, if appropriate, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ VI or VIIa in an excess based on VII or VIa.

Those starting materials required for the preparation of the compounds I which are not already known from the literature [WO-A 95/20,569; WO-A 94/24,085; Synlett (1) (1995) 32-33; Synlett (4) (1996) 356-357; J.Gen.Chem.USSR 59 (1989) 264-272; Heterocycles 31 (1990) 1543-1548; Tetrahedron 49 (1993) 49-64; J.Chem.Res.Miniprint 11 (1980) 4658-4667] can be prepared in accordance with the literature cited.

2B. The reaction of the compound VIII with the oxime derivative IV is carried out in a manner known per se at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent in the presence of a base.

Suitable solvents are alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably dimethyl sulfoxide, dimethylformamide and dimethylacetamide. Mixtures of these can also be used.

Bases which are suitable are, generally, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, and also alkali metal alkoxides and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Potassium tert-butoxide, sodium methoxide and potassium carbonate are especially preferred.

In general, the bases are used in equimolar amounts, in an excess or, if appropriate, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ IV in an excess based on VIII.

2.1 In accordance with the above-described reaction conditions, the compounds Ia, Ib and Ic are also especially preferably obtained by first converting the pyridine VIa with the oxime IV into the corresponding derivative VIIIa and subsequently reacting VIIIa with VIIa to give Ia, Ib or Ic.

3. The compounds of the formula I where R is C(CONHCH₃)═NOCH₃ are advantageously obtained by reacting a compound of the formula Ic in a manner known per se with methylamine or a salt thereof (IX).

Z⁻ in formula IX is the anion of an inorganic acid, especially a halide anion, in particular chloride.

This reaction is carried out in a manner known per se (EP-A 477 631) at from 0° C. to 150° C., preferably 10° C. to 100° C., in an inert organic solvent and in the presence or absence of a base.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably tetrahydrofuran. Mixtures of these can also be used.

Suitable bases are, generally, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal oxides and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, furthermore organic bases, eg. tertiary amines such as trimethylamine, triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Tertiary amines are especially preferred.

The bases are generally used in equimolar amounts, in an excess or, if appropriate, as the solvent.

In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ IX in an excess based on Ic.

The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude product. In some cases, the intermediates and end products are obtained in the form of colorless or pale brown viscous oils which are freed from volatile components or purified under reduced pressure and at moderately elevated temperatures. If the intermediates and end products are obtained as solids, they can also be purified by recrystallization or digestion.

In the definitions of the symbols given in the above formulae, collective terms were used which generally represent the following substituents:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 10 carbon atoms, eg. C₁-C₆-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

Haloalkyl: straight-chain or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms (as mentioned above), it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, eg. C₁-C₂-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

Alkylcarbonyl: an alkyl group having 1 to 6 or 10 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (—CO—);

Alkylsulfonyl: a straight-chain or branched alkyl group having 1 to 6 or 10 carbon atoms (as mentioned above) which is bonded to the skeleton via a sulfonyl group (—SO₂—);

Alkylsulfoxyl: a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a sulfoxyl group (—SO₃—);

Alkoxy: straight-chain or branched alkyl groups having 1 to 4 or 6 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (—O—);

Haloalkoxy: straight-chain or branched haloalkyl groups having 1 to 4, 6 or 10 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (—O—);

Alkoxycarbonyl: an alkoxy group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (—CO—);

Alkoxyimino: straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxyimino group (—ON=);

Alkylthio: straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above) which are bonded to the skeleton via a sulfur atom (—S—);

Alkylamino: a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via an amino group (—NH—);

Dialkylamino: two straight-chain or branched alkyl groups, independent of one another, which have in each case 1 to 6 carbon atoms (as mentioned above) and are bonded to the skeleton via a nitrogen atom;

Alkylaminocarbonyl: an alkylamino group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (—CO—);

Dialkylaminocarbonyl: a dialkylamino group having two C₁-C₆-alkyl groups (as mentioned above), independent of one another, which is bonded to the skeleton via a carbonyl group (—CO—);

Alkylaminothiocarbonyl: an alkylamino group having 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a thiocarbonyl group (—CS—);

Dialkylaminothiocarbonyl: a dialkylamino group having two C₁-C₆-alkyl groups (as mentioned above), independent of one another, which is bonded to the skeleton via a thiocarbonyl group (—CS—);

Alkenyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 6 or 10 carbon atoms and a double bond in any position, eg. C₂-C₆-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, l-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

Alkenyloxy: unsaturated straight-chain or branched hydrocarbon radicals having 3 to 6 or 10 carbon atoms and a double bond in any position which is not adjacent to the hetero atom (as mentioned above) which are bonded to the skeleton via an oxygen atom (—O—);

Alkenylcarbonyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a double bond in any position (as mentioned above) which are bonded to the skeleton via a carbonyl group (—CO—);

Alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 6, 8 or 10 carbon atoms and a triple bond in any position, eg. C₂-C₆-alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

Alkynyloxy: unsaturated straight-chain or branched hydrocarbon radicals having 3 to 10 carbon atoms and a triple bond in any position which is not adjacent to the hetero atom (as mentioned above) which are bonded to the skeleton via an oxygen atom (—O—);

Alkynylcarbonyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a triple bond in any position (as mentioned above) which are bonded to the skeleton via a carbonyl group (—CO—);

Cycloalkyl: monocyclic saturated hydrocarbon groups having 3 to 6 or 10 carbon ring members, eg. C₃-C₈-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;

Cycloalkoxy: monocyclic saturated hydrocarbon groups having 3 to 6 or 10 carbon ring members (as mentioned above) which are bonded to the skeleton via an oxygen atom (—O—);

Cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having 3 to 6 or 10 carbon ring members and a double bond in any position of the ring, eg. C₅-C₈-cycloalkenyl such as cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl;

Heterocyclyl: 5- or 6-membered heterocycles containing, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, eg. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2,3-pyrrolin-2-yl, 2,3-pyrrolin-3-yl, 2,4-pyrrolin-2-yl, 2,4-pyrrolin-3-yl, 2,3-isoxazolin-3-yl, 3,4-isoxazolin-3-yl, 4,5-isoxazolin-3-yl, 2,3-isoxazolin-4-yl, 3,4-isoxazolin-4-yl, 4,5-isoxazolin-4-yl, 2,3-isoxazolin-5-yl, 3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl, 3,4-isothiazolin-3-yl, 4,5-isothiazolin-3-yl, 2,3-isothiazolin-4-yl, 3,4-isothiazolin-4-yl, 4,5-isothiazolin-4-yl, 2,3-isothiazolin-5-yl, 3,4-isothiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl and 1,2,4-tetrahydrotriazin-3-yl;

Heterocyclyloxy: 5- or 6-membered heterocycles (as mentioned above) which are bonded to the skeleton via an oxygen atom (—O—);

Aryl: a mono- to trinuclear aromatic ring system containing 6 to 14 carbon ring members, eg. phenyl, naphthyl and anthracenyl;

Aryloxy: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via an oxygen atom (—O—);

Arylthio: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfur atom (—S—);

Arylcarbonyl: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a carbonyl group (—CO—);

Arylsulfonyl: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfonyl group (—SO₂—);

Arylsulfoxyl: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfoxyl group (—O—SO₂—);

Hetaryl: a mono- or binuclear, 5-, 6-, 9- or 10-membered aromatic ring system which, in addition to carbon ring members, contains hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen: eg.

5-membered hetaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom: 5-membered hetaryl ring groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;

benzo-fused 5-membered hetaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulfur atom: 5-membered hetaryl ring groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group;

5-membered hetaryl, bonded via nitrogen and containing one to four nitrogen atoms, or benzo-fused 5-membered hetaryl, bonded via nitrogen and containing one to three nitrogen atoms: 5-membered hetaryl ring groups which, in addition to carbon atoms, can contain one to four nitrogen atoms, or one to three nitrogen atoms, as ring members and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the skeleton via one of the nitrogen ring members;

6-membered hetaryl containing one to three. or one to four, nitrogen atoms: 6-membered hetaryl ring groups which, in addition to carbon atoms, can contain one to three, or one to four, nitrogen atoms as ring members, eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl;

Hetaryloxy: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via an oxygen atom (—O—);

Hetarylthio: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfur atom (—S—);

Hetarylcarbonyl: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a carbonyl group (—CO—);

Hetarylsulfonyl: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfonyl group (—SO₂—).

Hetarylsulfoxyl: a mono- or binuclear heteroaromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfoxyl group (—O—SO₂—).

The addition “unsubstituted or substituted” when relating to alkyl, alkenyl and alkynyl groups is intended to express that these groups can be partially or fully halogenated [ie. some or all of the hydrogen atoms of these groups can be replaced by identical or different halogen atoms as mentioned above (preferably fluorine, chlorine or bromine)] and/or can have attached to them one to three (preferably one) of the following radicals:

cyano, nitro, hydroxyl, amino, formyl, carboxyl, aminocarbonyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino and alkylcarbonyl-N-alkylamino, the alkyl groups in these radicals preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms;

cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino, unsubstituted or substituted by customary groups, the cyclic systems containing 3 to 12 ring members, preferably 2 to 8 ring members, in particular 3 to 6 ring members and the alkyl groups in these radicals containing preferably 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms;

aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, arylalkyl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, hetarylalkoxy, hetarylalkylthio, hetarylalkylamino and hetarylalkyl-N-alkylamino, unsubstituted or substituted by customary groups, the aryl radicals preferably containing 6 to 10 ring members, in particular 6 ring members (phenyl), the hetaryl radicals containing in particular 5 or 6 ring members and the alkyl groups in these radicals containing preferably 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms.

The addition “unsubstituted or substituted” when relating to the cyclic (saturated, unsaturated or aromatic) groups is intended to express that these groups can be partially or fully halogenated [ie. some or all of the hydrogen atoms of these groups can be replaced by identical or different halogen atoms as mentioned above (preferably fluorine, chlorine or bromine, in particular fluorine or chlorine)] and/or can have attached to them one to four (in particular one to three) of the following radicals:

cyano, nitro, hydroxyl, amino, carboxyl, aminocarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkynyl, haloalkynyl, alkynyloxy, haloalkynyloxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino and alkylcarbonyl-N-alkylamino, the alkyl groups in these radicals preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms and the alkenyl or alkynyl groups mentioned in these radicals containing 2 to 8, preferably 2 to 6, in particular 2 to 4 carbon atoms;

and/or one to three (in particular one) of the following radicals:

cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino, unsubstituted or substituted by customary groups, the cyclic systems containing 3 to 12 ring members, preferably 2 to 8 ring members, in particular 3 to 6 ring members and the alkyl groups in these radicals containing preferably 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms;

aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy, arylalkylthio, arylalkylamino, arylalkyl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, hetaryl-N-alkylamino, hetarylalkoxy, hetarylalkylthio, hetarylalkylamino and hetarylalkyl-N-alkylamino, unsubstituted or substituted by customary groups, the aryl radicals containing preferably 6 to 10 ring members, in particular 6 ring members (phenyl), the hetaryl radicals containing in particular 5 or 6 ring members and the alkyl groups in these radicals containing preferably 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms,

and/or one or two (in particular one) of the following radicals:

formyl,

CR^(v)=NOR^(vi) [where R^(v) is hydrogen, alkyl, cycloalkyl and aryl and R^(vi) is alkyl, alkenyl, haloalkenyl, alkynyl and arylalkyl (the alkyl groups mentioned preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, and the cycloalkyl groups, alkenyl groups and alkynyl groups mentioned preferably containing 3 to 8, in particular 3 to 6, carbon atoms) and aryl, in particular phenyl, which is unsubstituted or which can be substituted by customary groups] or

NR^(vii)-CO-D-R^(viii) [where R^(vii) is hydrogen, hydroxyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkoxy and C₁-C₆-alkoxycarbonyl, R^(viii) is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, aryl, aryl-C₁-C₆-alkyl, hetaryl and hetaryl-C₁-C₆-alkyl and D is a direct bond, oxygen or nitrogen, it being possible for the nitrogen to have attached to it one of the groups mentioned for R^(vi)],

and/or where two adjacent C atoms of the cyclic systems can have attached to them a C₃-C₅-alkylene, C₃-C₅-alkenylene, oxy-C₂-C₄-alkylene, oxy-C₁-C₃-alkyleneoxy, oxy-C₂-C₄-alkenylene, oxy-C₂-C₄-alkenyleneoxy or butadienediyl group, it being possible for these bridges, in turn, to be partially or fully halogenated and/or to have attached to them one to three, in particular one or two, of the following radicals:

C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and C₁-C₄-alkylthio.

Customary groups are to be understood as meaning, in particular, the following substituents: cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino and C₁-C₄-alkylthio.

Preferred compounds of the formula I with a view to their biological activities are those where R² has the following meanings:

alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy, it being possible for the hydrocarbon groups, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following radicals:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, amino thiocarbonyl,

C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkylcarbonyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminorothicaboyl di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyloxy,

benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, it being possible for the aromatic rings to be substituted by customary groups;

cycloalkyl, cycloalkoxy, heterocyclyl or heterocyclyloxy, it being possible for the cyclic groups, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following radicals:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, amino thiocarbonyl,

C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkylcarbonyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy,

benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, it being possible for the aromatic rings to be substituted by customary groups;

aryl, hetaryl, aryloxy or hetaryloxy, it being possible for the cyclic groups, in turn, to be partially or fully halogenated and/or to have attached to them one to three of the following radicals:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,

C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkylcarbonyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy,

benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy, it being possible for the aromatic rings to be substituted by customary groups,

C(═NOR^(i))—A_(m)—R^(ii) or NR^(iii)—CO—D—R^(iv);

A is oxygen, sulfur or nitrogen, the nitrogen having attached to it hydrogen or C₁-C₆-alkyl;

m is 0 or 1;

R^(i) is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R^(ii) is hydrogen or C₁-C₆-alkyl;

D is a direct bond, oxygen or NR^(b) (R^(b)=hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, aryl, aryl-C₁-C₆-alkyl, hetaryl and hetaryl-C₁-C₆-alkyl);

R^(iii) is hydrogen, hydroxyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkoxy and C₁-C₆-alkoxycarbonyl;

R^(iv) is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, aryl, aryl-C₁-C₆-alkyl, hetaryl and hetaryl-C₁-C₆-alkyl.

Especially preferred pyridine derivatives of the formula I are those where the substituents have the following meanings:

R¹ is hydrogen, cyano,

C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,

aryl, aryl-C₁-C₄-alkyl and aryloxy-C₁-C₄-alkyl, it being possible for the aromatic rings to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, and C(CH₃)═N—A¹—R^(a);

R² is unsubstituted or substituted aryl, hetaryl, aryloxy, hetaryloxy, arylthio and hetarylthio;

—Q—C(R³)═N—Y¹—R⁴ or —Q—O—N═CR⁵R⁶,

R¹ and R² together with the carbon atom to which they are bonded are a four- to eight-membered ring which, in addition to carbon atoms, can contain one or two oxygen and/or sulfur atoms and/or NH and/or N(C₁-C₄-alkyl) groups and whose carbon atoms can have attached to them one of the following substituents: halogen, C₁-C₆-alkyl or C₁-C₄-alkoxyimino, where

R¹ and R² are not simultaneously bonded to the carbon atoms via hetero atoms.

Moreover, preferred pyridine derivatives of the formula I are those where the substituents have the following meanings:

R¹ is hydrogen, cyano, halogen,

C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl,

aryl, aryl-C₁-C₄-alkyl, aryloxy-C₁-C₄-alkyl and aryl-C₁-C₄-alkoxy, it being possible for the aromatic rings to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, and C(CH₃)═N—A¹—R^(a);

R² is unsubstituted or substituted aryl and hetaryl;

—Q—C(R³)═N—Y¹—R⁴ or —Q—O—N═CR⁵R⁶,

R¹ and R² are not simultaneously bonded to the carbon atom via hetero atoms.

Especially preferred with a view to biological efficacy are compounds I where the radical R and the group —Y—N═CR¹R² are bonded to adjacent C atoms of the pyridyl ring.

Moreover, especially preferred compounds I are those where n is 0 or 1.

In the event that n is 1, preferred compounds I are those where X is cyano, halogen (in particular fluorine and chlorine), C₁-C₃-alkyl (in particular methyl and ethyl), C₁-C₂-haloalkyl (in particular difluoromethyl and trifluoromethyl), C₁-C₃-alkoxy (in particular methoxy), C₁-C₂-haloalkoxy (in particular difluoromethoxy and trifluoromethoxy) or cyclopropyl.

Moreover, especially preferred compounds I are those where Y is oxygen.

In the event that Y is nitrogen, preferred compounds I are those where the nitrogen atom additionally has attached to it a hydrogen atom or a C₁-C₃-alkyl group (in particular methyl, ethyl or isopropyl).

Additionally preferred compounds I are those where R is C(CO₂CH₃)═CHCH₃, C(CO₂CH₃)═CHOCH₃, C(CO₂CH₃)═NOCH₃ or C(CONHCH₃)═NOCH₃.

The following compounds Ia.1-Id.4 are particularly preferred.

Particularly preferred with a view to use against animal pests and harmful fungi are compounds of the formula I.4

where substituents and the index have the following meanngs:

R is C(CO₂CH₃)═CHCH₃, C(CO₂CH₃)═CHOCH₃, C(CO₂CH₃)═NOCH₃ or C(CONHCH₃)═NOCH₃;

X is cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl;

n is 0 or 1;

R¹ is hydrogen, hydroxyl, cyano, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, or benzyl which can be substituted by customary groups;

R² is hydrogen, C₃-C₆-cycloalkyl,

C₁-C₆-alkyl or C₁-C₆-alkoxy which can be partially or fully halogenated and/or can have attached to it one to three (in particular one) of the following groups: cyano, C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, or phenyl, naphthyl, pyridinyl, pyrazinyl, thienyl, pyrazolyl or isoxazolyl, in each case unsubstituted or substituted by customary groups;

phenyl, naphthyl, pyridinyl, pyrazinyl, thienyl, pyrazolyl or isoxazolyl, unsubstituted or substituted by customary groups;

phenoxy, naphthyloxy, pyridinyloxy, pyrazinyloxy, thienyloxy, pyrazolyloxy or isoxazolyloxy, unsubstituted or substituted by customary groups; or

R¹ and R² together with the carbon atom to which they are bonded are a saturated or partially unsaturated, four- to eight-membered ring which, in addition to hydrocarbon ring members, can contain a hetero atom selected from the group consisting of oxygen, sulfur and nitrogen and which can be partially halogenated and/or can have attached to it one to three of the following groups: C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, oxo (═O) and C₁-C₄-alkoxyimino (═N-alkoxy), where

R¹ and R² are not simultaneously bonded to the carbon atom via hetero atoms;

Moreover, particularly preferred with a view to use against animal pests and harmful fungi are compounds of the formula I.8

where the substituents and the index have the following meanings:

R is C(CO₂CH₃)═CHCH₃, C(CO₂CH₃)═CHOCH₃, C(CO₂CH₃)═NOCH₃ or C(CONHCH₃)═NOCH₃;

X is cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl;

n is 0 or 1;

R¹ is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl;

R³ is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl;

Y¹ is O, NH or N(CH₃);

R⁴ is hydrogen,

C₁-C₆-alkyl which can have attached to it one of the following groups: C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, unsubstituted or substituted by customary groups, or phenyl, unsubstituted or substituted by customary groups;

C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, or C₃-C₆-cycloalkyl, unsubstituted or substituted by customary groups.

Furthermore, particularly preferred with a view to use against animal pests and harmful fungi are compounds of the formula I.12

where the substituents and the index have the following meanings:

R is C(CO₂CH₃)═CHCH₃, C(CO₂CH₃)═CHOCH₃, C(CO₂CH₃)═NOCH₃ or C(CONHCH₃)═NOCH₃;

X is cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl;

n is 0 or 1;

R¹ is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl;

R^(x) is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl;

R^(y) is hydrogen,

C₁-C₆-alkyl which can be partially or fully halogenated and/or can have attached to it one to three (in particular one) of the following groups: C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, unsubstituted or substituted by customary groups, or phenyl, unsubstituted or substituted by customary groups;

C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,

C₃-C₆-cycloalkyl, unsubstituted or substituted by customary groups; phenyl, unsubstituted or substituted by customary groups, pyridyl, unsubstituted or substituted by customary groups, or pyrimidyl, unsubstituted or substituted by customary groups;

R^(z) is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl and C₃-C₆-cycloalkyl, or

R^(y) and R^(x) together with the double bond to which they are bonded are C₄-C₆-cycloalkenyl.

Particularly preferred with a view to their use are the compounds I compiled in the tables which follow. Moreover, the groups mentioned in the tables for a substituent are, in their own right and independent of the combination in which they are mentioned, an especially preferred embodiment of the substituent in question.

Table 1

Compounds of the formula Ia.1 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 2

Compounds of the formula Ia.2 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 3

Compounds of the formula Ia.3 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 4

Compounds of the formula Ia.4 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 5

Compounds of the formula Ia.4 where X_(n) is 6-CF₃ and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 6

Compounds of the formula Ia.4 where X_(n) is 6-CH(CH₃)₂ and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 7

Compounds of the formula Ib.1 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 8

Compounds of the formula Ib.2 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 9

Compounds of the formula Ib.3 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 10

Compounds of the formula Ib.4 where X_(n) is hydrogen and the comination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 11

Compounds of the formula Ib.4 where X_(n) is 6-CF₃ and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 12

Compounds of the formula Ib.4 where X_(n) is 6-CH(CH₃)₂ and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 13

Compounds of the formula Ic.1 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 14

Compounds of the formula Ic.2 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 15

Compounds of the formula Ic.3 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 16

Compounds of the formula Ic.4 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 17

Compounds of the formula Ic.4 where X_(n) is 6-CF₃ and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 18

Compounds of the formula Ic.4 where X_(n) is 6-CH(CH₃)₂ and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 19

Compounds of the formula Id.1 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 20

Compounds of the formula Id.2 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 21

Compounds of the formula Id.3 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 22

Compounds of the formula Id.4 where X_(n) is hydrogen and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 23

Compounds of the formula Id.4 where X_(n) is 6-CF₃ and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 24

Compounds of the formula Id.4 where X_(n) is 6-CH(CH₃)₂ and the combination of the radicals R¹ and R² for each compound corresponds to one line of Table A

Table 25

Compounds of the formula Ia.5 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 26

Compounds of the formula Ia.5 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 27

Compounds of the formula Ia.5 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 28

Compounds of the formula Ia.6 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 29

Compounds of the formula Ia.6 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 30

Compounds of the formula Ia.6 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 31

Compounds of the formula Ia.7 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 32

Compounds of the formula Ia.7 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 33

Compounds of the formula Ia.7 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 34

Compounds of the formula Ia.8 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 35

Compounds of the formula Ia.8 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 36

Compounds of the formula Ia.8 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 37

Compounds of the formula Ia.8 where X_(n) is 6-CF₃, Y¹ is oxygen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 38

Compounds of the formula Ia.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 39

Compounds of the formula Ia.8 where X_(n) is 6-CF₃, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 40

Compounds of the formula Ia.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 41

Compounds of the formula Ia.8 where X_(n) is 6-CF₃, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 42

Compounds of the formula Ia.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 43

Compounds of the formula Ib.5 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 44

Compounds of the formula Ib.5 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 45

Compounds of the formula Ib.5 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 46

Compounds of the formula Ib.6 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 47

Compounds of the formula Ib.6 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 48

Compounds of the formula Ib.6 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 49

Compounds of the formula Ib.7 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 50

Compounds of the formula Ib.7 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 51

Compounds of the formula Ib.7 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 52

Compounds of the formula Ib.8 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 53

Compounds of the formula Ib.8 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 54

Compounds of the formula Ib.8 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 55

Compounds of the formula Ib.8 where X_(n) is 6-CF₃, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 56

Compounds of the formula Ib.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 57

Compounds of the formula Ib.8 where X_(n) is 6-CF₃, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 58

Compounds of the formula Ib.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 59

Compounds of the formula Ib.8 where X_(n) is 6-CF₃, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 60

Compounds of the formula Ib.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 61

Compounds of the formula Ic.5 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 62

Compounds of the formula Ic.5 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 63

Compounds of the formula Ic.5 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 64

Compounds of the formula Ic.6 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 65

Compounds of the formula Ic.6 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 66

Compounds of the formula Ic.6 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 67

Compounds of the formula Ic.7 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 68

Compounds of the formula Ic.7 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 69

Compounds of the formula Ic.7 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 70

Compounds of the formula Ic.8 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 71

Compounds of the formula Ic.8 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 72

Compounds of the formula Ic.8 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 73

Compounds of the formula Ic.8 where X_(n) is 6-CF₃, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 74

Compounds of the formula Ic.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 75

Compounds of the formula Ic.8 where X_(n) is 6-CF₃, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 76

Compounds of the formula Ic.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 77

Compounds of the formula Ic.8 where X_(n) is 6-CF₃, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 78

Compounds of the formula Ic.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 79

Compounds of the formula Id.5 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 80

Compounds of the formula Id.5 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 81

Compounds of the formula Id.5 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 82

Compounds of the formula Id.6 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 83

Compounds of the formula Id.6 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 84

Compounds of the formula Id.6 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 85

Compounds of the formula Id.7 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 86

Compounds of the formula Id.7 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 87

Compounds of the formula Id.7 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 88

Compounds of the formula Id.8 where X_(n) is hydrogen, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 89

Compounds of the formula Id.8 where X_(n) is hydrogen, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 90

Compounds of the formula Id.8 where X_(n) is hydrogen, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 91

Compounds of the formula Id.8 where X_(n) is 6-CF₃, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 92

Compounds of the formula Id.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is oxygen and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 93

Compounds of the formula Id.8 where X_(n) is 6-CF₃, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 94

Compounds of the formula Id.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is NH and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 95

Compounds of the formula Id.8 where X_(n) is 6-CF₃, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 96

Compounds of the formula Id.8 where X_(n) is 6-CH(CH₃)₂, Y¹ is NCH₃ and the combination of the radicals R¹, R³ and R⁴ for each compound corresponds to one line of Table B

Table 97

Compounds of the formula Ia.9 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 98

Compounds of the formula Ia.10 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 99

Compounds of the formula Ia.11 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 100

Compounds of the formula Ia.12 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 101

Compounds of the formula Ia.12 where X_(n) is 6-CF₃ and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 102

Compounds of the formula Ia.12 where X_(n) is 6-CH(CH₃)₂ and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 103

Compounds of the formula Ib.9 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 104

Compounds of the formula Ib.10 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 105

Compounds of the formula Ib.11 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 106

Compounds of the formula Ib.12 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 107

Compounds of the formula Ib.12 where X_(n) is 6-CF₃ and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 108

Compounds of the formula Ib.12 where X_(n) is 6-CH(CH₃)₂ and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 109

Compounds of the formula Ic.9 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 110

Compounds of the formula Ic.10 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 111

Compounds of the formula Ic.11 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 112

Compounds of the formula Ic.12 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 113

Compounds of the formula Ic.12 where X_(n) is 6-CF₃ and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 114

Compounds of the formula Ic.12 where X_(n) is 6-CH(CH₃)₂ and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 115

Compounds of the formula Id.9 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 116

Compounds of the formula Id.10 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 117

Compounds of the formula Id.11 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 118

Compounds of the formula Id.12 where X_(n) is hydrogen and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 119

Compounds of the formula Id.12 where X_(n) is 6-CF₃ and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

Table 120

Compounds of the formula Id.12 where X_(n) is 6-CH(CH₃)₂ and the combination of the radicals R¹, R^(x), R^(y) and R^(z) for each compound corresponds to one line of Table C

TABLE A No. R¹ R² A.1 H CH₃ A.2 H CH₂CH₃ A.3 H CH₂CH₂CH₃ A.4 H CH(CH₃)₂ A.5 H CH₂CH₂CH₂CH₃ A.6 H C(CH₃)₃ A.7 H CH(CH₃)CH₂CH₃ A.8 H C₆H₅ A.9 H 2-F—C₆H₄ A.10 H 3-F—C₆H₄ A.11 H 4-F—C₆H₄ A.12 H 3-CH₃—C₆H₄ A.13 H 3-OCH₃—C₆H₄ A.14 H 3-CF₃—C₆H₄ A.15 H 3-Cl—C₆H₄ A.16 H 2-CH₃—C₆H₄ A.17 H 4-CH₃—C₆H₄ A.18 H cyclopropyl A.19 H cyclohexyl A.20 H CH₂CH₂Cl A.21 H CH₂CH₂CH₂CN A.22 H CH₂—C₆H₅ A.23 H CH₂CH₂CH₂CH₂—OCH₃ A.24 H CH₂CH₂—OCH₂CH₃ A.25 H CH₂C(CH₃)═NOCH₃ A.26 H CH₂-[4-F—C₆H₄] A.27 H CH₂-[3-CN—C₆H₄] A.28 H 3-CN—C₆H₄ A.29 H 3,5-(CH₃)₂—C₆H₃ A.30 H 3-COCH₃—C₆H₄ A.31 H 3-[C(CH₃)═NOCH₃]—C₆H₄ A.32 H 1-naphthyl A.33 H CH₂CH₂—O—C₆H₅ A.34 H CH₂—(3-Cl-pyridin-5-yl] A.35 H 4-OCH₃-pyridin-2-yl A.36 H CH₂—[5-Cl-pyrazin-2-yl] A.37 H 2-thienyl A.38 H 3-CH(CH₃)₂-isoxazol-5-yl A.39 H 3-C₆H₅-pyrazol-1-yl A.40 H OCH(CH₃)₂ A.41 H OCH₂CH₂CH₂CH₂CH₃ A.42 H O-[4-F—C₆H₄] A.43 H OCH₂-[4-F—C₆H₄] A.44 H O-[6-CH₃-pyridin-2-yl] A.45 H O—CO-[4-Cl—C₆H₄] A.46 H NH-[4-Cl—C₆H₄] A.47 CH₃ CH₃ A.48 CH₃ CH₂CH₃ A.49 CH₃ CH₂CH₂CH₃ A.50 CH₃ CH(CH₃)₂ A.51 CH₃ CH₂CH₂CH₂CH₃ A.52 CH₃ C(CH₃)₃ A.53 CH₃ CH(CH₃)CH₂CH₃ A.54 CH₃ C₆H₅ A.55 CH₃ 2-F—C₆H₄ A.56 CH₃ 3-F—C₆H₄ A.57 CH₃ 4-F—C₆H₄ A.58 CH₃ 3-CH₃—C₆H₄ A.59 CH₃ 3-OCH₃—C₆H₄ A.60 CH₃ 3-CF₃—C₆H₄ A.61 CH₃ 3-Cl—C₆H₄ A.62 CH₃ 2-CH₃—C₆H₄ A.63 CH₃ 4-CH₃—C₆H₄ A.64 CH₃ cyclopropyl A.65 CH₃ cyclohexyl A.66 CH₃ CH₂CH₂Cl A.67 CH₃ CH₂CH₂CH₂CN A.68 CH₃ CH₂—C₆H₅ A.69 CH₃ CH₂CH₂CH₂CH₂—OCH₃ A.70 CH₃ CH₂CH₂—OCH₂CH₃ A.71 CH₃ CH₂C(CH₃)═NOCH₃ A.72 CH₃ CH₂-[4-F—C₆H₄] A.73 CH₃ CH₂-[3-CN—C₆H₄] A.147 CH₃ 3-CN—C₆H₄ A.148 CH₃ 3,5-(CH₃)₂—C₆H₃ A.149 CH₃ 3-COCH₃—C₆H₄ A.150 CH₃ 3-[C(CH₃)═NOCH₃]—C₆H₄ A.151 CH₃ 1-naphthyl A.152 CH₃ CH₂CH₂—O—C₆H₅ A.153 CH₃ CH₂-[3-Cl-pyridin-5-yl] A.154 CH₃ 4-OCH₃-pyridin-2-yl A.155 CH₃ CH₂-[5-Cl-pyrazin-2-yl] A.156 CH₃ 2-thienyl A.157 CH₃ 3-CH(CH₃)₂-isoxazol-5-yl A.158 CH₃ 3-C₆H₅-pyrazol-1-yl A.159 CH₃ OCH(CH₃)₂ A.160 CH₃ OCH₂CH₂CH₂CH₂CH₃ A.161 CH₃ O-[4-F—C₆H₄] A.162 CH₃ OCH₂-[4-F—C₆H₄] A.163 CH₃ O-[6-CH₃-pyridin-2-yl] A.164 CH₃ O—CO-[4-Cl—C₆H₄] A.165 CH₃ NH-[4-Cl—C₆H₄] A.166 OH CH₃ A.167 OH CH₂CH₂CH₂CH₃ A.168 OH CH(CH₃)₂ A.169 OH 3-CH₃—C₆H₄ A.170 OH CH₂—C₆H₅ A.171 OH 3,5-Cl₂—C₆H₃ A.172 OCH₃ CH₃ A.173 OCH₃ CH₂CH₂CH₂CH₃ A.174 OCH₃ CH(CH₃)₂ A.175 OCH₃ CH₂CH₂CH₂CH₂CH₂CH₃ A.176 OCH₃ 3-CH₃—C₆H₄ A.177 OCH₃ CH₂—C₆H₅ A.178 OCH₃ 3,5-Cl₂—C₆H₃ A.179 OCH₂CH₃ CH₃ A.180 OCH₂CH₃ CH₂CH₂CH₃ A.181 OCH₂CH₃ CH(CH₃)₂ A.182 OCH₂CH₃ CH₂CH₂CH₂CH₂CH₃ A.183 OCH₂CH₃ 3-CH₃—C₆H₄ A.184 OCH₂CH₃ CH₂-[4-F—C₆H₄] A.185 OCH₂CH₃ 2,4-F₂—C₆H₃ A.186 cyclopropyl CH₃ A.187 cyclopropyl CH₂CH₂CH₃ A.188 cyclopropyl OCH₂CH₃ A.189 cyclopropyl C₆H₅ A.190 Cl C₆H₅ A.191 Cl CH₃ A.192 Cl CH(CH₃)₂ A.193 Cl 3-CH₃—C₆H₄ A.194 Cl 3-CN—C₆H₄ A.195 Cl CH₂CH₂—O—C₆H₅ A.196 Cl CH₂CH₂—OCH₂CH₃ A.197 Cl CH₂-[4-F—C₆H₄] A.198 SCH₃ CH₃ A.199 SCH₃ C₆H₅ A.200 SCH₃ CH(CH₃)₂ A.201 CH(CH₃)₂ CH₃ A.202 CH(CH₃)₂ CH₂CH₃ A.203 CH(CH₃)₂ C₆H₅ A.204 CH(CH₃)₂ OCH₃ A.205 CH(CH₃)₂ OCH(CH₃)₂ A.206 CH(CH₃)₂ 3-CH₃—C₆H₄ A.207 CN CH₃ A.208 CN 3-CH₃—C₆H₄ A.209 CN CH₂-[2,4-Cl₂—C₆H₃] A.210 CN CH₂CH₂CH₂CH₃ A.211 CN CH(CH₃)₂ A.212 CH₂CH₃ CH₃ A.213 CH₂CH₃ CH₂CH₃ A.214 CH₂CH₃ CH₂CH₂CH₃ A.215 CH₂CH₃ CH(CH₃)₂ A.216 CH₂CH₃ CH₂CH₂CH₂CH₃ A.217 CH₂CH₃ C(CH₃)₃ A.218 CH₂CH₃ CH(CH₃)CH₂CH₃ A.219 CH₂CH₃ C₆H₅ A.220 CH₂CH₃ 2-F—C₆H₄ A.221 CH₂CH₃ 3-F—C₆H₄ A.222 CH₂CH₃ 4-F—C₆H₄ A.223 CH₂CH₃ 3-CH₃—C₆H₄ A.224 CH₂CH₃ 3-OCH₃—C₆H₄ A.225 CH₂CH₃ 3-CF₃—C₆H₄ A.226 CH₂CH₃ 3-Cl—C₆H₄ A.227 CH₂CH₃ 2-CH₃—C₆H₄ A.228 CH₂CH₃ 4-CH₃—C₆H₄ A.229 CH₂CH₃ cyclopropyl A.230 CH₂CH₃ cyclohexyl A.231 CH₂CH₃ CH₂CH₂Cl A.232 CH₂CH₃ CH₂CH₂CH₂CN A.233 CH₂CH₃ CH₂—C₆H₅ A.234 CH₂CH₃ CH₂CH₂CH₂CH₂—OCH₃ A.235 CH₂CH₃ CH₂CH₂—OCH₂CH₃ A.236 CH₂CH₃ CH₂C(CH₃)═NOCH₃ A.237 CH₂CH₃ CH₂-[4-F—C₆H₄] A.238 CH₂CH₃ CH₂-[3-CN—C₆H₄] A.239 CH₂CH₃ 3-CN—C₆H₄ A.240 CH₂CH₃ 3,5-(CH₃)₂—C₆H₃ A.241 CH₂CH₃ 3-COCH₃—C₆H₄ A.242 CH₂CH₃ 3-[C(CH₃)═NOCH₃]—C₆H₄ A.243 CH₂CH₃ 1-naphthyl A.244 CH₂CH₃ CH₂CH₂—O—C₆H₅ A.245 CH₂CH₃ CH₂-[3-Cl-pyridin-5-yl] A.246 CH₂CH₃ 4-OCH₃-pyridin-2-yl A.247 CH₂CH₃ CH₂-[5-Cl-pyrazin-2-yl] A.248 CH₂CH₃ 2-thienyl A.249 CH₂CH₃ 3-CH(CH₃)₂-isoxazol-5-yl A.250 CH₂CH₃ 3-C₆H₅-pyrazol-1-yl A.251 CH₂CH₃ OCH(CH₃)₂ A.252 CH₂CH₃ OCH₂CH₂CH₂CH₂CH₃ A.253 CH₂CH₃ O-[4-F—C₆H₄] A.254 CH₂CH₃ OCH₂-[4-F—C₆H₄] A.255 CH₂CH₃ O-[6-CH₃-pyridin-2-yl] A.256 CH₂CH₃ O—CO-[4-Cl—C₆H₄] A.257 CH₂CH₃ NH-[4-Cl—C₆H₄] A.258 CH₃ CH₂ON═C(CH₃)₂ A.259 CH₃ CH₂ON═C(CH₃)—CH₂CH₃ A.260 CH₃ CH₂ON═C(CH₃)—C₆H₅ A.261 CH₃ CH₂ON═C(CH₃)-[4-Cl—C₆H₄] A.262 CH₂CH₃ CH₂ON═C(CH₃)₂ A.263 CH₂CH₃ CH₂ON═C(CH₃)—CH₂CH₃ A.264 CH₂CH₃ CH₂ON═C(CH₃)—C₆H₅ A.265 CH₂CH₃ CH₂ON═C(CH₃)-[4-Cl—C₆H₄] A.266 CH₂—C₆H₅ CH₂ON═C(CH₃)₂ A.267 CH₂—C₆H₅ CH₂ON═C(CH₃)—CH₂CH₃ A.268 CH₂—C₆H₅ CH₂ON═C(CH₃)—C₆H₅ A.269 CH₂—C₆H₅ CH₂ON═C(CH₃)-[4-Cl—C₆H₄] A.270 H CH═CH—C₆H₅ A.271 H CH═C(CH₃)—C₆H₅ A.272 H CH═CCl—C₆H₅ A.273 H C(CH₃)═CH—C₆H₅ A.274 H CCl═CH—C₆H₅ A.275 H CH═CH-[4-F—C₆H₄] A.276 H CH═C(CH₃)-[4-F—C₆H₄] A.277 H CH═CCl-[4-F—C₆H₄] A.278 H CCl═CH-[4-F—C₆H₄] A.279 H C(CH₃)═CH-[4-F—C₆H₄] A.280 CH₃ CH═CH—C₆H₅ A.281 CH₃ CH═C(CH₃)—C₆H₅ A.282 CH₃ CH═CCl—C₆H₅ A.283 CH₃ C(CH₃)═CH—C₆H₅ A.284 CH₃ CCl═CH—C₆H₅ A.285 CH₃ CH═CH-[4-F—C₆H₄] A.286 CH₃ CH═C(CH₃)-[4-F—C₆H₄] A.287 CH₃ CH═CCl-[4-F—C₆H₄] A.288 CH₃ CCl═CH-[4-F—C₆H₄] A.289 CH₃ C(CH₃)═CH-[4-F—C₆H₄] A.290 CH₂CH₃ CH═CH—C₆H₅ A.291 CH₂CH₃ CH═C(CH₃)—C₆H₅ A.292 CH₂CH₃ CH═CCl—C₆H₅ A.293 CH₂CH₃ C(CH₃)═CH—C₆H₅ A.294 CH₂CH₃ CCl═CH—C₆H₅ A.295 CH₂CH₃ CH═CH-[4-F—C₆H₄] A.296 CH₂CH₃ CH═C(CH₃)-[4-F—C₆H₄] A.297 CH₂CH₃ CH═CCl-[4-F—C₆H₄] A.298 CH₂CH₃ CCl═CH-[4-F—C₆H₄] A.299 CH₂CH₃ C(CH₃)═CH-[4-F—C₆H₄] A.300 CH₂—C₆H₅ CH═CH—C₆H₅ A.301 CH₂—C₆H₅ CH═C(CH₃)—C₆H₅ A.302 CH₂—C₆H₅ CH═CCl—C₆H₅ A.303 CH₂—C₆H₅ C(CH₃)═CH—C₆H₅ A.304 CH₂—C₆H₅ CCl═CH—C₆H₅ A.305 CH₂—C₆H₅ CH═CH-[4-F—C₆H₄] A.306 CH₂—C₆H₅ CH═C(CH₃)-[4-F—C₆H₄] A.307 CH₂—C₆H₅ CH═CCl-[4-F—C₆H₄] A.308 CH₂—C₆H₅ CCl═CH-[4-F—C₆H₄] A.309 CH₂—C₆H₅ C(CH₃)═CH-[4-F—C₆H₄] A.310 H CH(CH₃)—C(CH₃)═NOCH₃ A.311 H CH(CH₃)—C(CH₃)═NOCH₂CH₃ A.312 H CH(CH₃)—C₆H₅ A.313 H CH(CH₃)-[4-F—C₆H₄] A.314 H 1-C₆H₅-cyclopropyl A.315 H 1-[4-Cl—C₆H₄]-cyclopropyl A.316 H CH₂C(CH₃)═NOCH₃ A.317 H CH₂C(CH₃)═NOCH₂CH₃ A.318 H 1-[C(CH₃)═NOCH₃)-cyclopropyl A.319 CH₃ CH(CH₃)—C(CH₃)═NOCH₃ A.320 CH₃ CH(CH₃)—C(CH₃)═NOCH₂CH₃ A.321 CH₃ CH(CH₃)—C₆H₅ A.322 CH₃ CH(CH₃)-[4-F—C₆H₄] A.323 CH₃ 1-C₆H₅-cyclopropyl A.324 CH₃ 1-[4-Cl—C₆H₄]-cyclopropyl A.325 CH₃ CH₂C(CH₃)═NOCH₃ A.326 CH₃ CH₂C(CH₃)═NOCH₂CH₃ A.327 CH₃ 1-[C(CH₃)═NOCH₃]-cyclopropyl A.328 CH₂CH₃ CH(CH₃)—C(CH₃)═NOCH₃ A.329 CH₂CH₃ CH(CH₃)—C(CH₃)═NOCH₂CH₃ A.330 CH₂CH₃ CH(CH₃)—C₆H₅ A.331 CH₂CH₃ CH(CH₃)-[4-F—C₆H₄] A.332 CH₂CH₃ 1-C₆H₅-cyclopropyl A.333 CH₂CH₃ 1-[4-Cl—C₆H₄)-cyclopropyl A.334 CH₂CH₃ CH₂C(CH₃)═NOCH₃ A.335 CH₂CH₃ CH₂C(CH₃)═NOCH₂CH₃ A.336 CH₂CH₃ 1-[C(CH₃)═NOCH₃]-cyclopropyl A.337 CH₂—C₆H₅ CH(CH₃)—C(CH₃)═NOCH₃ A.338 CH₂—C₆H₅ CH(CH₃)—C(CH₃)═NOCH₂CH₃ A.339 CH₂—C₆H₅ CH(CH₃)—C₆H₅ A.340 CH₂—C₆H₅ CH(CH₃)-[4-F—C₆H₄] A.341 CH₂—C₆H₅ 1-C₆H₅-cyclopropyl A.342 CH₂—C₆H₅ 1-[4-Cl—C₆H₄]-cyclopropyl A.343 CH₂—C₆H₅ CH₂C(CH₃)═NOCH₃ A.344 CH₂—C₆H₅ CH₂C(CH₃)═NOCH₂CH₃ A.345 CH₂—C₆H₅ 1-[C(CH₃)═NOCH₃]-cyclopropyl A.346 —(CH₂)₄— A.347 —(CH₂)₅— A.348 —(CH₂)₂—O—(CH₂)₂— A.349 —(CH₂)₂—S—(CH₂)₂— A.350 —(CH₂)₂—CH(CH₃)—(CH₂)₂— A.351 —(CH₂)₂—C(═O)—(CH₂)₂— A.352 —(CH₂)₂—C(═NOCH₃)—(CH₂)₂— A.353 —(CH₂)₂—C(OCH₃)₂—(CH₂)₂— A.354 —CH₂—CH(CH₃)—CH₂—CH(CH₃)—CH₂— A.355 —(CH₂)₃—CH(CH₃)—CH₂— A.356 —CH═CH—C(═NOCH₃)—CH═CH— A.357 —CH₂—C(═NOCH₃)—(CH₂)₃— A.358 CH₃ CF₃ A.359 H CF₃ A.360 CF₃ CH₃ A.361 CF₃ H

TABLE B No. R¹ R³ R⁴ B.1 Cl H H B.2 Cl CH₃ H B.3 Cl CH₂CH₃ H B.4 Cl CF₃ H B.5 Cl CHF₂ H B.6 Cl CH₂F H B.7 Cl Cl H B.8 Cl OCH₃ H B.9 Cl OCH₂CH₃ H B.10 Cl CN H B.11 CH₃ H H B.12 CH₃ CH₃ H B.13 CH₃ CH₂CH₃ H B.14 CH₃ CF₃ H B.15 CH₃ CHF₂ H B.16 CH₃ CH₂F H B.17 CH₃ Cl H B.18 CH₃ OCH₃ H B.19 CH₃ OCH₂CH₃ H B.20 CH₃ CN H B.21 CF₃ H H B.22 CF₃ CH₃ H B.23 CF₃ CH₂CH₃ H B.24 CF₃ CF₃ H B.25 CF₃ CHF₂ H B.26 CF₃ CH₂F H B.27 CF₃ Cl H B.28 CF₃ OCH₃ H B.29 CF₃ OCH₂CH₃ H B.30 CF₃ CN H B.31 Cl H CH₃ B.32 Cl CH₃ CH₃ B.33 Cl CH₂CH₃ CH₃ B.34 Cl CF₃ CH₃ B.35 Cl CHF₂ CH₃ B.36 Cl CH₂F CH₃ B.37 Cl Cl CH₃ B.38 Cl OCH₃ CH₃ B.39 Cl OCH₂CH₃ CH₃ B.40 Cl CN CH₃ B.41 CH₃ H CH₃ B.42 CH₃ CH₃ CH₃ B.43 CH₃ CH₂CH₃ CH₃ B.44 CH₃ CF₃ CH₃ B.45 CH₃ CHF₂ CH₃ B.46 CH₃ CH₂F CH₃ B.47 CH₃ Cl CH₃ B.48 CH₃ OCH₃ CH₃ B.49 CH₃ OCH₂CH₃ CH₃ B.50 CH₃ CN CH₃ B.51 CF₃ H CH₃ B.52 CF₃ CH₃ CH₃ B.53 CF₃ CH₂CH₃ CH₃ B.54 CF₃ CF₃ CH₃ B.55 CF₃ CHF₂ CH₃ B.56 CF₃ CH₂F CH₃ B.57 CF₃ Cl CH₃ B.58 CF₃ OCH₃ CH₃ B.59 CF₃ OCH₂CH₃ CH₃ B.60 CF₃ CN CH₃ B.61 Cl H CH₂CH₃ B.62 Cl CH₃ CH₂CH₃ B.63 Cl CH₂CH₃ CH₂CH₃ B.64 Cl CF₃ CH₂CH₃ B.65 Cl CHF₂ CH₂CH₃ B.66 Cl CH₂F CH₂CH₃ B.67 Cl Cl CH₂CH₃ B.68 Cl OCH₃ CH₂CH₃ B.69 Cl OCH₂CH₃ CH₂CH₃ B.70 Cl CN CH₂CH₃ B.71 CH₃ H CH₂CH₃ B.72 CH₃ CH₃ CH₂CH₃ B.73 CH₃ CH₂CH₃ CH₂CH₃ B.74 CH₃ CF₃ CH₂CH₃ B.75 CH₃ CHF₂ CH₂CH₃ B.76 CH₃ CH₂F CH₂CH₃ B.77 CH₃ Cl CH₂CH₃ B.78 CH₃ OCH₃ CH₂CH₃ B.79 CH₃ OCH₂CH₃ CH₂CH₃ B.80 CH₃ CN CH₂CH₃ B.81 CF₃ H CH₂CH₃ B.82 CF₃ CH₃ CH₂CH₃ B.83 CF₃ CH₂CH₃ CH₂CH₃ B.84 CF₃ CF₃ CH₂CH₃ B.85 CF₃ CHF₂ CH₂CH₃ B.86 CF₃ CH₂F CH₂CH₃ B.87 CF₃ Cl CH₂CH₃ B.88 CF₃ OCH₃ CH₂CH₃ B.89 CF₃ OCH₂CH₃ CH₂CH₃ B.90 CF₃ CN CH₂CH₃ B.91 Cl H CH₂CH₂CH₃ B.92 Cl CH₃ CH₂CH₂CH₃ B.93 Cl CH₂CH₃ CH₂CH₂CH₃ B.94 Cl CF₃ CH₂CH₂CH₃ B.95 Cl CHF₂ CH₂CH₂CH₃ B.96 Cl CH₂F CH₂CH₂CH₃ B.97 Cl Cl CH₂CH₂CH₃ B.98 Cl OCH₃ CH₂CH₂CH₃ B.99 Cl OCH₂CH₃ CH₂CH₂CH₃ B.100 Cl CN CH₂CH₂CH₃ B.101 CH₃ H CH₂CH₂CH₃ B.102 CH₃ CH₃ CH₂CH₂CH₃ B.103 CH₃ CH₂CH₃ CH₂CH₂CH₃ B.104 CH₃ CF₃ CH₂CH₂CH₃ B.105 CH₃ CHF₂ CH₂CH₂CH₃ B.106 CH₃ CH₂F CH₂CH₂CH₃ B.107 CH₃ Cl CH₂CH₂CH₃ B.108 CH₃ OCH₃ CH₂CH₂CH₃ B.109 CH₃ OCH₂CH₃ CH₂CH₂CH₃ B.110 CH₃ CN CH₂CH₂CH₃ B.111 CF₃ H CH₂CH₂CH₃ B.112 CF₃ CH₃ CH₂CH₂CH₃ B.113 CF₃ CH₂CH₃ CH₂CH₂CH₃ B.114 CF₃ CF₃ CH₂CH₂CH₃ B.115 CF₃ CHF₂ CH₂CH₂CH₃ B.116 CF₃ CH₂F CH₂CH₂CH₃ B.117 CF₃ Cl CH₂CH₂CH₃ B.118 CF₃ OCH₃ CH₂CH₂CH₃ B.119 CF₃ OCH₂CH₃ CH₂CH₂CH₃ B.120 CF₃ CN CH₂CH₂CH₃ B.121 Cl H CH(CH₃)₂ B.122 Cl CH₃ CH(CH₃)₂ B.123 Cl CH₂CH₃ CH(CH₃)₂ B.124 Cl CF₃ CH(CH₃)₂ B.125 Cl CHF₂ CH(CH₃)₂ B.126 Cl CH₂F CH(CH₃)₂ B.127 Cl Cl CH(CH₃)₂ B.128 Cl OCH₃ CH(CH₃)₂ B.129 Cl OCH₂CH₃ CH(CH₃)₂ B.130 Cl CN CH(CH₃)₂ B.131 CH₃ H CH(CH₃)₂ B.132 CH₃ CH₃ CH(CH₃)₂ B.133 CH₃ CH₂CH₃ CH(CH₃)₂ B.134 CH₃ CF₃ CH(CH₃)₂ B.135 CH₃ CHF₂ CH(CH₃)₂ B.136 CH₃ CH₂F CH(CH₃)₂ B.137 CH₃ Cl CH(CH₃)₂ B.138 CH₃ OCH₃ CH(CH₃)₂ B.139 CH₃ OCH₂CH₃ CH(CH₃)₂ B.140 CH₃ CN CH(CH₃)₂ B.141 CF₃ H CH(CH₃)₂ B.142 CF₃ CH₃ CH(CH₃)₂ B.143 CF₃ CH₂CH₃ CH(CH₃)₂ B.144 CF₃ CF₃ CH(CH₃)₂ B.145 CF₃ CHF₂ CH(CH₃)₂ B.146 CF₃ CH₂F CH(CH₃)₂ B.147 CF₃ Cl CH(CH₃)₂ B.148 CF₃ OCH₃ CH(CH₃)₂ B.149 CF₃ OCH₂CH₃ CH(CH₃)₂ B.150 CF₃ CN CH(CH₃)₂ B.151 Cl H CH₂CH═CH₂ B.152 Cl CH₃ CH₂CH═CH₂ B.153 Cl CH₂CH₃ CH₂CH═CH₂ B.154 Cl CF₃ CH₂CH═CH₂ B.155 Cl CHF₂ CH₂CH═CH₂ B.156 Cl CH₂F CH₂CH═CH₂ B.157 Cl Cl CH₂CH═CH₂ B.158 Cl OCH₃ CH₂CH═CH₂ B.159 Cl OCH₂CH₃ CH₂CH═CH₂ B.160 Cl CN CH₂CH═CH₂ B.161 CH₃ H CH₂CH═CH₂ B.162 CH₃ CH₃ CH₂CH═CH₂ B.163 CH₃ CH₂CH₃ CH₂CH═CH₂ B.164 CH₃ CF₃ CH₂CH═CH₂ B.165 CH₃ CHF₂ CH₂CH═CH₂ B.166 CH₃ CH₂F CH₂CH═CH₂ B.167 CH₃ Cl CH₂CH═CH₂ B.168 CH₃ OCH₃ CH₂CH═CH₂ B.169 CH₃ OCH₂CH₃ CH₂CH═CH₂ B.170 CH₃ CN CH₂CH═CH₂ B.171 CF₃ H CH₂CH═CH₂ B.172 CF₃ CH₃ CH₂CH═CH₂ B.173 CF₃ CH₂CH₃ CH₂CH═CH₂ B.174 CF₃ CF₃ CH₂CH═CH₂ B.175 CF₃ CHF₂ CH₂CH═CH₂ B.176 CF₃ CH₂F CH₂CH═CH₂ B.177 CF₃ Cl CH₂CH═CH₂ B.178 CF₃ OCH₃ CH₂CH═CH₂ B.179 CF₃ OCH₂CH₃ CH₂CH═CH₂ B.180 CF₃ CN CH₂CH═CH₂ B.181 Cl H CH₂CH═CH—Cl (trans) B.182 Cl CH₃ CH₂CH═CH—Cl (trans) B.183 Cl CH₂CH₃ CH₂CH═CH—Cl (trans) B.184 Cl CF₃ CH₂CH═CH—Cl (trans) B.185 Cl CHF₂ CH₂CH═CH—Cl (trans) B.186 Cl CH₂F CH₂CH═CH—Cl (trans) B.187 Cl Cl CH₂CH═CH—Cl (trans) B.188 Cl OCH₃ CH₂CH═CH—Cl (trans) B.189 Cl OCH₂CH₃ CH₂CH═CH—Cl (trans) B.190 Cl CN CH₂CH═CH—Cl (trans) B.191 CH₃ H CH₂CH═CH—Cl (trans) B.192 CH₃ CH₃ CH₂CH═CH—Cl (trans) B.193 CH₃ CH₂CH₃ CH₂CH═CH—Cl (trans) B.194 CH₃ CF₃ CH₂CH═CH—Cl (trans) B.195 CH₃ CHF₂ CH₂CH═CH—Cl (trans) B.196 CH₃ CH₂F CH₂CH═CH—Cl (transY B.197 CH₃ Cl CH₂CH═CH—Cl (trans) B.198 CH₃ OCH₃ CH₂CH═CH—Cl (trans) B.199 CH₃ OCH₂CH₃ CH₂CH═CH—Cl (trans) B.200 CH₃ CN CH₂CH═CH—Cl (trans) B.201 CF₃ H CH₂CH═CH—Cl (trans) B.202 CF₃ CH₃ CH₂CH═CH—Cl (trans) B.203 CF₃ CH₂CH₃ CH₂CH═CH—Cl (trans) B.204 CF₃ CF₃ CH₂CH═CH—Cl (trans) B.205 CF₃ CHF₂ CH₂CH═CH—Cl (trans) B.206 CF₃ CH₂F CH₂CH═CH—Cl (trans) B.207 CF₃ Cl CH₂CH═CH—Cl (trans) B.208 CF₃ OCH₃ CH₂CH═CH—Cl (trans) B.209 CF₃ OCH₂CH₃ CH₂CH═CH—Cl (trans) B.210 CF₃ CN CH₂CH═CH—Cl (trans) B.211 Cl H CH₂CCl═CH₂ B.212 Cl CH₃ CH₂CCl═CH₂ B.213 Cl CH₂CH₃ CH₂CCl═CH₂ B.214 Cl CF₃ CH₂CCl═CH₂ B.215 Cl CHF₂ CH₂CCl═CH₂ B.216 Cl CH₂F CH₂CCl═CH₂ B.217 Cl Cl CH₂CCl═CH₂ B.218 Cl OCH₃ CH₂CCl═CH₂ B.219 Cl OCH₂CH₃ CH₂CCl═CH₂ B.220 Cl CN CH₂CCl═CH₂ B.221 CH₃ H CH₂CCl═CH₂ B.222 CH₃ CH₃ CH₂CCl═CH₂ B.223 CH₃ CH₂CH₃ CH₂CCl═CH₂ B.224 CH₃ CF₃ CH₂CCl═CH₂ B.225 CH₃ CHF₂ CH₂CCl═CH₂ B.226 CH₃ CH₂F CH₂CCl═CH₂ B.227 CH₃ Cl CH₂CCl═CH₂ B.228 CH₃ OCH₃ CH₂CCl═CH₂ B.229 CH₃ OCH₂CH₃ CH₂CCl═CH₂ B.230 CH₃ CN CH₂CCl═CH₂ B.231 CF₃ H CH₂CCl═CH₂ B.232 CF₃ CH₃ CH₂CCl═CH₂ B.233 CF₃ CH₂CH₃ CH₂CCl═CH₂ B.234 CF₃ CF₃ CH₂CCl═CH₂ B.235 CF₃ CHF₂ CH₂CCl═CH₂ B.236 CF₃ CH₂F CH₂CCl═CH₂ B.237 CF₃ Cl CH₂CCl═CH₂ B.238 CF₃ OCH₃ CH₂CCl═CH₂ B.239 CF₃ OCH₂CH₃ CH₂CCl═CH₂ B.240 CF₃ CN CH₂CCl═CH₂ B.241 Cl H CH₂C≡CH B.242 Cl CH₃ CH₂C≡CH B.243 Cl CH₂CH₃ CH₂C≡CH B.244 Cl CF₃ CH₂C≡CH B.245 Cl CHF₂ CH₂C≡CH B.246 Cl CH₂F CH₂C≡CH B.247 Cl Cl CH₂C≡CH B.248 Cl OCH₃ CH₂C≡CH B.249 Cl OCH₂CH₃ CH₂C≡CH B.250 Cl CN CH₂C≡CH B.251 CH₃ H CH₂C≡CH B.252 CH₃ CH₃ CH₂C≡CH B.253 CH₃ CH₂CH₃ CH₂C≡CH B.254 CH₃ CF₃ CH₂C≡CH B.255 CH₃ CHF₂ CH₂C≡CH B.256 CH₃ CH₂F CH₂C≡CH B.257 CH₃ Cl CH₂C≡CH B.258 CH₃ OCH₃ CH₂C≡CH B.259 CH₃ OCH₂CH₃ CH₂C≡CH B.260 CH₃ CN CH₂C≡CH B.261 CF₃ H CH₂C≡CH B.262 CF₃ CH₃ CH₂C≡CH B.263 CF₃ CH₂CH₃ CH₂C≡CH B.264 CF₃ CF₃ CH₂C≡CH B.265 CF₃ CHF₂ CH₂C≡CH B.266 CF₃ CH₂F CH₂C≡CH B.267 CF₃ Cl CH₂C≡CH B.268 CF₃ OCH₃ CH₂C≡CH B.269 CF₃ OCH₂CH₃ CH₂C≡CH B.270 CF₃ CN CH₂C≡CH B.271 Cl H CH₂C≡CCH₃ B.272 Cl CH₃ CH₂C≡CCH₃ B.273 Cl CH₂CH₃ CH₂C≡CCH₃ B.274 Cl CF₃ CH₂C≡CCH₃ B.275 Cl CHF₂ CH₂C≡CCH₃ B.276 Cl CH₂F CH₂C≡CCH₃ B.277 Cl Cl CH₂C≡CCH₃ B.278 Cl OCH₃ CH₂C≡CCH₃ B.279 Cl OCH₂CH₃ CH₂C≡CCH₃ B.280 Cl CN CH₂C≡CCH₃ B.281 CH₃ H CH₂C≡CCH₃ B.282 CH₃ CH₃ CH₂C≡CCH₃ B.283 CH₃ CH₂CH₃ CH₂C≡CCH₃ B.284 CH₃ CF₃ CH₂C≡CCH₃ B.285 CH₃ CHF₂ CH₂C≡CCH₃ B.286 CH₃ CH₂F CH₂C≡CCH₃ B.287 CH₃ Cl CH₂C≡CCH₃ B.288 CH₃ OCH₃ CH₂C≡CCH₃ B.289 CH₃ OCH₂CH₃ CH₂C≡CCH₃ B.290 CH₃ CN CH₂C≡CCH₃ B.291 CF₃ H CH₂C≡CCH₃ B.292 CF₃ CH₃ CH₂C≡CCH₃ B.293 CF₃ CH₂CH₃ CH₂C≡CCH₃ B.294 CF₃ CF₃ CH₂C≡CCH₃ B.295 CF₃ CHF₂ CH₂C≡CCH₃ B.296 CF₃ CH₂F CH₂C≡CCH₃ B.297 CF₃ Cl CH₂C≡CCH₃ B.298 CF₃ OCH₃ CH₂C≡CCH₃ B.299 CF₃ OCH₂CH₃ CH₂C≡CCH₃ B.300 CF₃ CN CH₂C≡CCH₃ B.301 Cl H CH₂C≡C—I B.302 Cl CH₃ CH₂C≡C—I B.303 Cl CH₂CH₃ CH₂C≡C—I B.304 Cl CF₃ CH₂C≡C—I B.305 Cl CHF₂ CH₂C≡C—I B.306 Cl CH₂F CH₂C≡C—I B.307 Cl Cl CH₂C≡C—I B.308 Cl OCH₃ CH₂C≡C—I B.309 Cl OCH₂CH₃ CH₂C≡C—I B.310 Cl CN CH₂C≡C—I B.311 CH₃ H CH₂C≡C—I B.312 CH₃ CH₃ CH₂C≡C—I B.313 CH₃ CH₂CH₃ CH₂C≡C—I B.314 CH₃ CF₃ CH₂C≡C—I B.315 CH₃ CHF₂ CH₂C≡C—I B.316 CH₃ CH₂F CH₂C≡C—I B.317 CH₃ Cl CH₂C≡C—I B.318 CH₃ OCH₃ CH₂C≡C—I B.319 CH₃ OCH₂CH₃ CH₂C≡C—I B.320 CH₃ CN CH₂C≡C—I B.321 CF₃ H CH₂C≡C—I B.322 CF₃ CH₃ CH₂C≡C—I B.323 CF₃ CH₂CH₃ CH₂C≡C—I B.324 CF₃ CF₃ CH₂C≡C—I B.325 CF₃ CHF₂ CH₂C≡C—I B.326 CF₃ CH₂F CH₂C≡C—I B.327 CF₃ Cl CH₂C≡C—I B.328 CF₃ OCH₃ CH₂C≡C—I B.329 CF₃ OCH₂CH₃ CH₂C≡C—I B.330 CF₃ CN CH₂C≡C—I B.331 Cl H CH(CH₃)C≡CH B.332 Cl CH₃ CH(CH₃)C≡CH B.333 Cl CH₂CH₃ CH(CH₃)C≡CH B.334 Cl CF₃ CH(CH₃)C≡CH B.335 Cl CHF₂ CH(CH₃)C≡CH B.336 Cl CH₂F CH(CH₃)C≡CH B.337 Cl Cl CH(CH₃)C≡CH B.338 Cl OCH₃ CH(CH₃)C≡CH B.339 Cl OCH₂CH₃ CH(CH₃)C≡CH B.340 Cl CN CH(CH₃)C≡CH B.341 CH₃ H CH(CH₃)C≡CH B.342 CH₃ CH₃ CH(CH₃)C≡CH B.343 CH₃ CH₂CH₃ CH(CH₃)C≡CH B.344 CH₃ CF₃ CH(CH₃)C≡CH B.345 CH₃ CHF₂ CH(CH₃)C≡CH B.346 CH₃ CH₂F CH(CH₃)C≡CH B.347 CH₃ Cl CH(CH₃)C≡CH B.348 CH₃ OCH₃ CH(CH₃)C≡CH B.349 CH₃ OCH₂CH₃ CH(CH₃)C≡CH B.350 CH₃ CN CH(CH₃)C≡CH B.351 CF₃ H CH(CH₃)C≡CH B.352 CF₃ CH₃ CH(CH₃)C≡CH B.353 CF₃ CH₂CH₃ CH(CH₃)C≡CH B.354 CF₃ CF₃ CH(CH₃)C≡CH B.355 CF₃ CHF₂ CH(CH₃)C≡CH B.356 CF₃ CH₂F CH(CH₃)C≡CH B.357 CF₃ Cl CH(CH₃)C≡CH B.358 CF₃ OCH₃ CH(CH₃)C≡CH B.359 CF₃ OCH₂CH₃ CH(CH₃)C≡CH B.360 CF₃ CN CH(CH₃)C≡CH B.361 Cl H CH₂CH₂—O—CH₂CH₃ B.362 Cl CH₃ CH₂CH₂—O—CH₂CH₃ B.363 Cl CH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.364 Cl CF₃ CH₂CH₂—O—CH₂CH₃ B.365 Cl CHF₂ CH₂CH₂—O—CH₂CH₃ B.366 Cl CH₂F CH₂CH₂—O—CH₂CH₃ B.367 Cl Cl CH₂CH₂—O—CH₂CH₃ B.368 Cl OCH₃ CH₂CH₂—O—CH₂CH₃ B.369 Cl OCH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.370 Cl CN CH₂CH₂—O—CH₂CH₃ B.371 CH₃ H CH₂CH₂—O—CH₂CH₃ B.372 CH₃ CH₃ CH₂CH₂—O—CH₂CH₃ B.373 CH₃ CH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.374 CH₃ CF₃ CH₂CH₂—O—CH₂CH₃ B.375 CH₃ CHF₂ CH₂CH₂—O—CH₂CH₃ B.376 CH₃ CH₂F CH₂CH₂—O—CH₂CH₃ B.377 CH₃ Cl CH₂CH₂—O—CH₂CH₃ B.378 CH₃ OCH₃ CH₂CH₂—O—CH₂CH₃ B.379 CH₃ OCH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.380 CH₃ CN CH₂CH₂—O—CH₂CH₃ B.381 CF₃ H CH₂CH₂—O—CH₂CH₃ B.382 CF₃ CH₃ CH₂CH₂—O—CH₂CH₃ B.383 CF₃ CH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.384 CF₃ CF₃ CH₂CH₂—O—CH₂CH₃ B.385 CF₃ CHF₂ CH₂CH₂—O—CH₂CH₃ B.386 CF₃ CH₂F CH₂CH₂—O—CH₂CH₃ B.387 CF₃ Cl CH₂CH₂—O—CH₂CH₃ B.388 CF₃ OCH₃ CH₂CH₂—O—CH₂CH₃ B.389 CF₃ OCH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.390 CF₃ CN CH₂CH₂—O—CH₂CH₃ B.391 Cl H CH₂—C₆H₅ B.392 Cl CH₃ CH₂—C₆H₅ B.393 Cl CH₂CH₃ CH₂—C₆H₅ B.394 Cl CF₃ CH₂—C₆H₅ B.395 Cl CHF₂ CH₂—C₆H₅ B.396 Cl CH₂F CH₂—C₆H₅ B.397 Cl Cl CH₂—C₆H₅ B.398 Cl OCH₃ CH₂—C₆H₅ B.399 Cl OCH₂CH₃ CH₂—C₆H₅ B.400 Cl CN CH₂—C₆H₅ B.401 CH₃ H CH₂—C₆H₅ B.402 CH₃ CH₃ CH₂—C₆H₅ B.403 CH₃ CH₂CH₃ CH₂—C₆H₅ B.404 CH₃ CF₃ CH₂—C₆H₅ B.405 CH₃ CHF₂ CH₂—C₆H₅ B.406 CH₃ CH₂F CH₂—C₆H₅ B.407 CH₃ Cl CH₂—C₆H₅ B.408 CH₃ OCH₃ CH₂—C₆H₅ B.409 CH₃ OCH₂CH₃ CH₂—C₆H₅ B.410 CH₃ CN CH₂—C₆H₅ B.411 CF₃ H CH₂—C₆H₅ B.412 CF₃ CH₃ CH₂—C₆H₅ B.413 CF₃ CH₂CH₃ CH₂—C₆H₅ B.414 CF₃ CF₃ CH₂—C₆H₅ B.415 CF₃ CHF₂ CH₂—C₆H₅ B.416 CF₃ CH₂F CH₂—C₆H₅ B.417 CF₃ Cl CH₂—C₆H₅ B.418 CF₃ OCH₃ CH₂—C₆H₅ B.419 CF₃ OCH₂CH₃ CH₂—C₆H₅ B.420 CF₃ CN CH₂—C₆H₅ B.421 Cl H cyclopropyl B.422 Cl CH₃ cyclopropyl B.423 Cl CH₂CH₃ cyclopropyl B.424 Cl CF₃ cyclopropyl B.425 Cl CHF₂ cyclopropyl B.426 Cl CH₂F cyclopropyl B.427 Cl Cl cyclopropyl B.428 Cl OCH₃ cyclopropyl B.429 Cl OCH₂CH₃ cyclopropyl B.430 Cl CN cyclopropyl B.431 CH₃ H cyclopropyl B.432 CH₃ CH₃ cyclopropyl B.433 CH₃ CH₂CH₃ cyclopropyl B.434 CH₃ CF₃ cyclopropyl B.435 CH₃ CHF₂ cyclopropyl B.436 CH₃ CH₂F cyclopropyl B.437 CH₃ Cl cyclopropyl B.438 CH₃ OCH₃ cyclopropyl B.439 CH₃ OCH₂CH₃ cyclopropyl B.440 CH₃ CN cyclopropyl B.441 CF₃ H cyclopropyl B.442 CF₃ CH₃ cyclopropyl B.443 CF₃ CH₂CH₃ cyclopropyl B.444 CF₃ CF₃ cyclopropyl B.445 CF₃ CHF₂ cyclopropyl B.446 CF₃ CH₂F cyclopropyl B.447 CF₃ Cl cyclopropyl B.448 CF₃ OCH₃ cyclopropyl B.449 CF₃ OCH₂CH₃ cyclopropyl B.450 CF₃ CN cyclopropyl B.451 Cl H CH₂-(2,2-Cl₂-cyclopropyl) B.452 Cl CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.453 Cl CH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.454 Cl CF₃ CH₂-(2,2-Cl₂-cyclopropyl) B.455 Cl CHF₂ CH₂-(2,2-Cl₂-cyclopropyl) B.456 Cl CH₂F CH₂-(2,2-Cl₂-cyclopropyl) B.457 Cl Cl CH₂-(2,2-Cl₂-cyclopropyl) B.458 Cl OCH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.459 Cl OCH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.460 Cl CN CH₂-(2,2-Cl₂-cyclopropyl) B.461 CH₃ H CH₂-(2,2-Cl₂-cyclopropyl) B.462 CH₃ CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.463 CH₃ CH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.464 CH₃ CF₃ CH₂-(2,2-Cl₂-cyclopropyl) B.465 CH₃ CHF₂ CH₂-(2,2-Cl₂-cyclopropyl) B.466 CH₃ CH₂F CH₂-(2,2-Cl₂-cyclopropyl) B.467 CH₃ Cl CH₂-(2,2-Cl₂-cyclopropyl) B.468 CH₃ OCH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.469 CH₃ OCH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.470 CH₃ CN CH₂-(2,2-Cl₂-cyclopropyl) B.471 CF₃ H CH₂-(2,2-Cl₂-cyclopropyl) B.472 CF₃ CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.473 CF₃ CH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.474 CF₃ CF₃ CH₂-(2,2-Cl₂-cyclopropyl) B.475 CF₃ CHF₂ CH₂-(2,2-Cl₂-cyclopropyl) B.476 CF₃ CH₂F CH₂-(2,2-Cl₂-cyclopropyl) B.477 CF₃ Cl CH₂-(2,2-Cl₂-cyclopropyl) B.478 CF₃ OCH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.479 CF₃ OCH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.480 CF₃ CN CH₂-(2,2-Cl₂-cyclopropyl) B.481 H CH₃ H B.482 H CH₂CH₃ H B.483 H CF₃ H B.484 H Cl H B.485 H OCH₃ H B.486 CH₂CH₃ CH₃ H B.487 CH₂CH₃ CH₂CH₃ H B.488 CH₂CH₃ CF₃ H B.489 CH₂CH₃ Cl H B.490 CH₂CH₃ OCH₃ H B.491 CHF₂ CH₃ H B.492 CHF₂ CH₂CH₃ H B.493 CHF₂ CF₃ H B.494 CHF₂ Cl H B.495 CHF₂ OCH₃ H B.496 CH₂F CH₃ H B.497 CH₂F CH₂CH₃ H B.498 CH₂F CF₃ H B.499 CH₂F Cl H B.500 CH₂F OCH₃ H B.501 OCH₃ CH₃ H B.502 OCH₃ CH₂CH₃ H B.503 OCH₃ CF₃ H B.504 OCH₃ Cl H B.505 OCH₃ OCH₃ H B.506 OCH₂CH₃ CH₃ H B.507 OCH₂CH₃ CH₂CH₃ H B.508 OCH₂CH₃ CF₃ H B.509 OCH₂CH₃ Cl H B.510 OCH₂CH₃ OCH₃ H B.511 CN CH₃ H B.512 CN CH₂CH₃ H B.513 CN CF₃ H B.514 CN Cl H B.515 CN OCH₃ H B.516 H CH₃ CH₃ B.517 H CH₂CH₃ CH₃ B.518 H CF₃ CH₃ B.519 H Cl CH₃ B.520 H OCH₃ CH₃ B.521 CH₂CH₃ CH₃ CH₃ B.522 CH₂CH₃ CH₂CH₃ CH₃ B.523 CH₂CH₃ CF₃ CH₃ B.524 CH₂CH₃ Cl CH₃ B.525 CH₂CH₃ OCH₃ CH₃ B.526 CHF₂ CH₃ CH₃ B.527 CHF₂ CH₂CH₃ CH₃ B.528 CHF₂ CF₃ CH₃ B.529 CHF₂ Cl CH₃ B.530 CHF₂ OCH₃ CH₃ B.531 CH₂F CH₃ CH₃ B.532 CH₂F CH₂CH₃ CH₃ B.533 CH₂F CF₃ CH₃ B.534 CH₂F Cl CH₃ B.535 CH₂F OCH₃ CH₃ B.536 OCH₃ CH₃ CH₃ B.537 OCH₃ CH₂CH₃ CH₃ B.538 OCH₃ CF₃ CH₃ B.539 OCH₃ Cl CH₃ B.540 OCH₃ OCH₃ CH₃ B.541 OCH₂CH₃ CH₃ CH₃ B.542 OCH₂CH₃ CH₂CH₃ CH₃ B.543 OCH₂CH₃ CF₃ CH₃ B.544 OCH₂CH₃ Cl CH₃ B.545 OCH₂CH₃ OCH₃ CH₃ B.546 CN CH₃ CH₃ B.547 CN CH₂CH₃ CH₃ B.548 CN CF₃ CH₃ B.549 CN Cl CH₃ B.550 CN OCH₃ CH₃ B.551 H CH₃ CH₂CH₃ B.552 H CH₂CH₃ CH₂CH₃ B.553 H CF₃ CH₂CH₃ B.554 H Cl CH₂CH₃ B.555 H OCH₃ CH₂CH₃ B.556 CH₂CH₃ CH₃ CH₂CH₃ B.557 CH₂CH₃ CH₂CH₃ CH₂CH₃ B.558 CH₂CH₃ CF₃ CH₂CH₃ B.559 CH₂CH₃ Cl CH₂CH₃ B.560 CH₂CH₃ OCH₃ CH₂CH₃ B.561 CHF₂ CH₃ CH₂CH₃ B.562 CHF₂ CH₂CH₃ CH₂CH₃ B.563 CHF₂ CF₃ CH₂CH₃ B.564 CHF₂ Cl CH₂CH₃ B.565 CHF₂ OCH₃ CH₂CH₃ B.566 CH₂F CH₃ CH₂CH₃ B.567 CH₂F CH₂CH₃ CH₂CH₃ B.568 CH₂F CF₃ CH₂CH₃ B.569 CH₂F Cl CH₂CH₃ B.570 CH₂F OCH₃ CH₂CH₃ B.571 OCH₃ CH₃ CH₂CH₃ B.572 OCH₃ CH₂CH₃ CH₂CH₃ B.573 OCH₃ CF₃ CH₂CH₃ B.574 OCH₃ Cl CH₂CH₃ B.575 OCH₃ OCH₃ CH₂CH₃ B.576 OCH₂CH₃ CH₃ CH₂CH₃ B.577 OCH₂CH₃ CH₂CH₃ CH₂CH₃ B.578 OCH₂CH₃ CF₃ CH₂CH₃ B.579 OCH₂CH₃ Cl CH₂CH₃ B.580 OCH₂CH₃ OCH₃ CH₂CH₃ B.581 CN CH₃ CH₂CH₃ B.582 CN CH₂CH₃ CH₂CH₃ B.583 CN CF₃ CH₂CH₃ B.584 CN Cl CH₂CH₃ B.585 CN OCH₃ CH₂CH₃ B.586 H CH₃ CH₂CH₂CH₃ B.587 H CH₂CH₃ CH₂CH₂CH₃ B.588 H CF₃ CH₂CH₂CH₃ B.589 H Cl CH₂CH₂CH₃ B.590 H OCH₃ CH₂CH₂CH₃ B.591 CH₂CH₃ CH₃ CH₂CH₂CH₃ B.592 CH₂CH₃ CH₂CH₃ CH₂CH₂CH₃ B.593 CH₂CH₃ CF₃ CH₂CH₂CH₃ B.594 CH₂CH₃ Cl CH₂CH₂CH₃ B.595 CH₂CH₃ OCH₃ CH₂CH₂CH₃ B.596 CHF₂ CH₃ CH₂CH₂CH₃ B.597 CHF₂ CH₂CH₃ CH₂CH₂CH₃ B.598 CHF₂ CF₃ CH₂CH₂CH₃ B.599 CHF₂ Cl CH₂CH₂CH₃ B.600 CHF₂ OCH₃ CH₂CH₂CH₃ B.601 CH₂F CH₃ CH₂CH₂CH₃ B.602 CH₂F CH₂CH₃ CH₂CH₂CH₃ B.603 CH₂F CF₃ CH₂CH₂CH₃ B.604 CH₂F Cl CH₂CH₂CH₃ B.605 CH₂F OCH₃ CH₂CH₂CH₃ B.606 OCH₃ CH₃ CH₂CH₂CH₃ B.607 OCH₃ CH₂CH₃ CH₂CH₂CH₃ B.608 OCH₃ CF₃ CH₂CH₂CH₃ B.609 OCH₃ Cl CH₂CH₂CH₃ B.610 OCH₃ OCH₃ CH₂CH₂CH₃ B.611 OCH₂CH₃ CH₃ CH₂CH₂CH₃ B.612 OCH₂CH₃ CH₂CH₃ CH₂CH₂CH₃ B.613 OCH₂CH₃ CF₃ CH₂CH₂CH₃ B.614 OCH₂CH₃ Cl CH₂CH₂CH₃ B.615 OCH₂CH₃ OCH₃ CH₂CH₂CH₃ B.616 CN CH₃ CH₂CH₂CH₃ B.617 CN CH₂CH₃ CH₂CH₂CH₃ B.618 CN CF₃ CH₂CH₂CH₃ B.619 CN Cl CH₂CH₂CH₃ B.620 CN OCH₃ CH₂CH₂CH₃ B.621 H CH₃ CH(CH₃)₂ B.622 H CH₂CH₃ CH(CH₃)₂ B.623 H CF₃ CH(CH₃)₂ B.624 H Cl CH(CH₃)₂ B.625 H OCH₃ CH(CH₃)₂ B.626 CH₂CH₃ CH₃ CH(CH₃)₂ B.627 CH₂CH₃ CH₂CH₃ CH(CH₃)₂ B.628 CH₂CH₃ CF₃ CH(CH₃)₂ B.629 CH₂CH₃ Cl CH(CH₃)₂ B.630 CH₂CH₃ OCH₃ CH(CH₃)₂ B.631 CHF₂ CH₃ CH(CH₃)₂ B.632 CHF₂ CH₂CH₃ CH(CH₃)₂ B.633 CHF₂ CF₃ CH(CH₃)₂ B.634 CHF₂ Cl CH(CH₃)₂ B.635 CHF₂ OCH₃ CH(CH₃)₂ B.636 CH₂F CH₃ CH(CH₃)₂ B.637 CH₂F CH₂CH₃ CH(CH₃)₂ B.638 CH₂F CF₃ CH(CH₃)₂ B.639 CH₂F Cl CH(CH₃)₂ B.640 CH₂F OCH₃ CH(CH₃)₂ B.641 OCH₃ CH₃ CH(CH₃)₂ B.642 OCH₃ CH₂CH₃ CH(CH₃)₂ B.643 OCH₃ CF₃ CH(CH₃)₂ B.644 OCH₃ Cl CH(CH₃)₂ B.645 OCH₃ OCH₃ CH(CH₃)₂ B.646 OCH₂CH₃ CH₃ CH(CH₃)₂ B.647 OCH₂CH₃ CH₂CH₃ CH(CH₃)₂ B.648 OCH₂CH₃ CF₃ CH(CH₃)₂ B.649 OCH₂CH₃ Cl CH(CH₃)₂ B.650 OCH₂CH₃ OCH₃ CH(CH₃)₂ B.651 CN CH₃ CH(CH₃)₂ B.652 CN CH₂CH₃ CH(CH₃)₂ B.653 CN CF₃ CH(CH₃)₂ B.654 CN Cl CH(CH₃)₂ B.655 CN OCH₃ CH(CH₃)₂ B.656 H CH₃ CH₂CH═CH₂ B.657 H CH₂CH₃ CH₂CH═CH₂ B.658 H CF₃ CH₂CH═CH₂ B.659 H Cl CH₂CH═CH₂ B.660 H OCH₃ CH₂CH═CH₂ B.661 CH₂CH₃ CH₃ CH₂CH═CH₂ B.662 CH₂CH₃ CH₂CH₃ CH₂CH═CH₂ B.663 CH₂CH₃ CF₃ CH₂CH═CH₂ B.664 CH₂CH₃ Cl CH₂CH═CH₂ B.665 CH₂CH₃ OCH₃ CH₂CH═CH₂ B.666 CHF₂ CH₃ CH₂CH═CH₂ B.667 CHF₂ CH₂CH₃ CH₂CH═CH₂ B.668 CHF₂ CF₃ CH₂CH═CH₂ B.669 CHF₂ Cl CH₂CH═CH₂ B.670 CHF₂ OCH₃ CH₂CH═CH₂ B.671 CH₂F CH₃ CH₂CH═CH₂ B.672 CH₂F CH₂CH₃ CH₂CH═CH₂ B.673 CH₂F CF₃ CH₂CH═CH₂ B.674 CH₂F Cl CH₂CH═CH₂ B.675 CH₂F OCH₃ CH₂CH═CH₂ B.676 OCH₃ CH₃ CH₂CH═CH₂ B.677 OCH₃ CH₂CH₃ CH₂CH═CH₂ B.678 OCH₃ CF₃ CH₂CH═CH₂ B.679 OCH₃ Cl CH₂CH═CH₂ B.680 OCH₃ OCH₃ CH₂CH═CH₂ B.681 OCH₂CH₃ CH₃ CH₂CH═CH₂ B.682 OCH₂CH₃ CH₂CH₃ CH₂CH═CH₂ B.683 OCH₂CH₃ CF₃ CH₂CH═CH₂ B.684 OCH₂CH₃ Cl CH₂CH═CH₂ B.685 OCH₂CH₃ OCH₃ CH₂CH═CH₂ B.686 CN CH₃ CH₂CH═CH₂ B.687 CN CH₂CH₃ CH₂CH═CH₂ B.688 CN CF₃ CH₂CH═CH₂ B.689 CN Cl CH₂CH═CH₂ B.690 CN OCH₃ CH₂CH═CH₂ B.691 H CH₃ CH₂CH═CH—Cl (trans) B.692 H CH₂CH₃ CH₂CH═CH—Cl (trans) B.693 H CF₃ CH₂CH═CH—Cl (trans) B.694 H Cl CH₂CH═CH—Cl (trans) B.695 H OCH₃ CH₂CH═CH—Cl (trans) B.696 CH₂CH₃ CH₃ CH₂CH═CH—Cl (trans) B.697 CH₂CH₃ CH₂CH₃ CH₂CH═CH—Cl (trans) B.698 CH₂CH₃ CF₃ CH₂CH═CH—Cl (trans) B.699 CH₂CH₃ Cl CH₂CH═CH—Cl (trans) B.700 CH₂CH₃ OCH₃ CH₂CH═CH—Cl (trans) B.701 CHF₂ CH₃ CH₂CH═CH—Cl (trans) B.702 CHF₂ CH₂CH₃ CH₂CH═CH—Cl (trans) B.703 CHF₂ CF₃ CH₂CH═CH—Cl (trans) B.704 CHF₂ Cl CH₂CH═CH—Cl (trans) B.705 CHF₂ OCH₃ CH₂CH═CH—Cl (trans) B.706 CH₂F CH₃ CH₂CH═CH—Cl (trans) B.707 CH₂F CH₂CH₃ CH₂CH═CH—Cl (trans) B.708 CH₂F CF₃ CH₂CH═CH—Cl (trans) B.709 CH₂F Cl CH₂CH═CH—Cl (trans) B.710 CH₂F OCH₃ CH₂CH═CH—Cl (trans) B.711 OCH₃ CH₃ CH₂CH═CH—Cl (trans) B.712 OCH₃ CH₂CH₃ CH₂CH═CH—Cl (trans) B.713 OCH₃ CF₃ CH₂CH═CH—Cl (trans) B.714 OCH₃ Cl CH₂CH═CH—Cl (trans) B.715 OCH₃ OCH₃ CH₂CH═CH—Cl (trans) B.716 OCH₂CH₃ CH₃ CH₂CH═CH—Cl (trans) B.717 OCH₂CH₃ CH₂CH₃ CH₂CH═CH—Cl (trans) B.718 OCH₂CH₃ CF₃ CH₂CH═CH—Cl (trans) B.719 OCH₂CH₃ Cl CH₂CH═CH—Cl (trans) B.720 OCH₂CH₃ OCH₃ CH₂CH═CH—Cl (trans) B.721 CN CH₃ CH₂CH═CH—Cl (trans) B.722 CN CH₂CH₃ CH₂CH═CH—Cl (trans) B.723 CN CF₃ CH₂CH═CH—Cl (trans) B.724 CN Cl CH₂CH═CH—Cl (trans) B.725 CN OCH₃ CH₂CH═CH—Cl (trans) B.726 H CH₃ CH₂CCl═CH₂ B.727 H CH₂CH₃ CH₂CCl═CH₂ B.728 H CF₃ CH₂CCl═CH₂ B.729 H Cl CH₂CCl═CH₂ B.730 H OCH₃ CH₂CCl═CH₂ B.731 CH₂CH₃ CH₃ CH₂CCl═CH₂ B.732 CH₂CH₃ CH₂CH₃ CH₂CCl═CH₂ B.733 CH₂CH₃ CF₃ CH₂CCl═CH₂ B.734 CH₂CH₃ Cl CH₂CCl═CH₂ B.735 CH₂CH₃ OCH₃ CH₂CCl═CH₂ B.736 CHF₂ CH₃ CH₂CCl═CH₂ B.737 CHF₂ CH₂CH₃ CH₂CCl═CH₂ B.738 CHF₂ CF₃ CH₂CCl═CH₂ B.739 CHF₂ Cl CH₂CCl═CH₂ B.740 CHF₂ OCH₃ CH₂CCl═CH₂ B.741 CH₂F CH₃ CH₂CCl═CH₂ B.742 CH₂F CH₂CH₃ CH₂CCl═CH₂ B.743 CH₂F CF₃ CH₂CCl═CH₂ B.744 CH₂F Cl CH₂CCl═CH₂ B.745 CH₂F OCH₃ CH₂CCl═CH₂ B.746 OCH₃ CH₃ CH₂CCl═CH₂ B.747 OCH₃ CH₂CH₃ CH₂CCl═CH₂ B.748 OCH₃ CF₃ CH₂CCl═CH₂ B.749 OCH₃ Cl CH₂CCl═CH₂ B.750 OCH₃ OCH₃ CH₂CCl═CH₂ B.751 OCH₂CH₃ CH₃ CH₂CCl═CH₂ B.752 OCH₂CH₃ CH₂CH₃ CH₂CCl═CH₂ B.753 OCH₂CH₃ CF₃ CH₂CCl═CH₂ B.754 OCH₂CH₃ Cl CH₂CCl═CH₂ B.755 OCH₂CH₃ OCH₃ CH₂CCl═CH₂ B.756 CN CH₃ CH₂CCl═CH₂ B.757 CN CH₂CH₃ CH₂CCl═CH₂ B.758 CN CF₃ CH₂CCl═CH₂ B.759 CN Cl CH₂CCl═CH₂ B.760 CN OCH₃ CH₂CCl═CH₂ B.761 H CH₃ CH₂C≡CH B.762 H CH₂CH₃ CH₂C≡CH B.763 H CF₃ CH₂C≡CH B.764 H Cl CH₂C≡CH B.765 H OCH₃ CH₂C≡CH B.766 CH₂CH₃ CH₃ CH₂C≡CH B.767 CH₂CH₃ CH₂CH₃ CH₂C≡CH B.768 CH₂CH₃ CF₃ CH₂C≡CH B.769 CH₂CH₃ Cl CH₂C≡CH B.770 CH₂CH₃ OCH₃ CH₂C≡CH B.771 CHF₂ CH₃ CH₂C≡CH B.772 CHF₂ CH₂CH₃ CH₂C≡CH B.773 CHF₂ CF₃ CH₂C≡CH B.774 CHF₂ Cl CH₂C≡CH B.775 CHF₂ OCH₃ CH₂C≡CH B.776 CH₂F CH₃ CH₂C≡CH B.777 CH₂F CH₂CH₃ CH₂C≡CH B.778 CH₂F CF₃ CH₂C≡CH B.779 CH₂F Cl CH₂C≡CH B.780 CH₂F OCH₃ CH₂C≡CH B.781 OCH₃ CH₃ CH₂C≡CH B.782 OCH₃ CH₂CH₃ CH₂C≡CH B.783 OCH₃ CF₃ CH₂C≡CH B.784 OCH₃ Cl CH₂C≡CH B.785 OCH₃ OCH₃ CH₂C≡CH B.786 OCH₂CH₃ CH₃ CH₂C≡CH B.787 OCH₂CH₃ CH₂CH₃ CH₂C≡CH B.788 OCH₂CH₃ CF₃ CH₂C≡CH B.789 OCH₂CH₃ Cl CH₂C≡CH B.790 OCH₂CH₃ OCH₃ CH₂C≡CH B.791 CN CH₃ CH₂C≡CH B.792 CN CH₂CH₃ CH₂C≡CH B.793 CN CF₃ CH₂C≡CH B.794 CN Cl CH₂C≡CH B.795 CN OCH₃ CH₂C≡CH B.796 H CH₃ CH₂C≡CCH₃ B.797 H CH₂CH₃ CH₂C≡CCH₃ B.798 H CF₃ CH₂C≡CCH₃ B.799 H Cl CH₂C≡CCH₃ B.800 H OCH₃ CH₂C≡CCH₃ B.801 CH₂CH₃ CH₃ CH₂C≡CCH₃ B.802 CH₂CH₃ CH₂CH₃ CH₂C≡CCH₃ B.803 CH₂CH₃ CF₃ CH₂C≡CCH₃ B.804 CH₂CH₃ Cl CH₂C≡CCH₃ B.805 CH₂CH₃ OCH₃ CH₂C≡CCH₃ B.806 CHF₂ CH₃ CH₂C≡CCH₃ B.807 CHF₂ CH₂CH₃ CH₂C≡CCH₃ B.808 CHF₂ CF₃ CH₂C≡CCH₃ B.809 CHF₂ Cl CH₂C≡CCH₃ B.810 CHF₂ OCH₃ CH₂C≡CCH₃ B.811 CH₂F CH₃ CH₂C≡CCH₃ B.812 CH₂F CH₂CH₃ CH₂C≡CCH₃ B.813 CH₂F CF₃ CH₂C≡CCH₃ B.814 CH₂F Cl CH₂C≡CCH₃ B.815 CH₂F OCH₃ CH₂C≡CCH₃ B.816 OCH₃ CH₃ CH₂C≡CCH₃ B.817 OCH₃ CH₂CH₃ CH₂C≡CCH₃ B.818 OCH₃ CF₃ CH₂C≡CCH₃ B.819 OCH₃ Cl CH₂C≡CCH₃ B.820 OCH₃ OCH₃ CH₂C≡CCH₃ B.821 OCH₂CH₃ CH₃ CH₂C≡CCH₃ B.822 OCH₂CH₃ CH₂CH₃ CH₂C≡CCH₃ B.823 OCH₂CH₃ CF₃ CH₂C≡CCH₃ B.824 OCH₂CH₃ Cl CH₂C≡CCH₃ B.825 OCH₂CH₃ OCH₃ CH₂C≡CCH₃ B.826 CN CH₃ CH₂C≡CCH₃ B.827 CN CH₂CH₃ CH₂C≡CCH₃ B.828 CN CF₃ CH₂C≡CCH₃ B.829 CN Cl CH₂C≡CCH₃ B.830 CN OCH₃ CH₂C≡CCH₃ B.831 H CH₃ CH₂C≡C—I B.832 H CH₂CH₃ CH₂C≡C—I B.833 H CF₃ CH₂C≡C—I B.834 H Cl CH₂C≡C—I B.835 H OCH₃ CH₂C≡C—I B.836 CH₂CH₃ CH₃ CH₂C≡C—I B.837 CH₂CH₃ CH₂CH₃ CH₂C≡C—I B.838 CH₂CH₃ CF₃ CH₂C≡C—I B.839 CH₂CH₃ Cl CH₂C≡C—I B.840 CH₂CH₃ OCH₃ CH₂C≡C—I B.841 CHF₂ CH₃ CH₂C≡C—I B.842 CHF₂ CH₂CH₃ CH₂C≡C—I B.843 CHF₂ CF₃ CH₂C≡C—I B.844 CHF₂ Cl CH₂C≡C—I B.845 CHF₂ OCH₃ CH₂C≡C—I B.846 CH₂F CH₃ CH₂C≡C—I B.847 CH₂F CH₂CH₃ CH₂C≡C—I B.848 CH₂F CF₃ CH₂C≡C—I B.849 CH₂F Cl CH₂C≡C—I B.850 CH₂F OCH₃ CH₂C≡C—I B.851 OCH₃ CH₃ CH₂C≡C—I B.852 OCH₃ CH₂CH₃ CH₂C≡C—I B.853 OCH₃ CF₃ CH₂C≡C—I B.854 OCH₃ Cl CH₂C≡C—I B.855 OCH₃ OCH₃ CH₂C≡C—I B.856 OCH₂CH₃ CH₃ CH₂C≡C—I B.857 OCH₂CH₃ CH₂CH₃ CH₂C≡C—I B.858 OCH₂CH₃ CF₃ CH₂C≡C—I B.859 OCH₂CH₃ Cl CH₂C≡C—I B.860 OCH₂CH₃ OCH₃ CH₂C≡C—I B.861 CN CH₃ CH₂C≡C—I B.862 CN CH₂CH₃ CH₂C≡C—I B.863 CN CF₃ CH₂C≡C—I B.864 CN Cl CH₂C≡C—I B.865 CN OCH₃ CH₂C≡C—I B.866 H CH₃ CH(CH₃)C≡CH B.867 H CH₂CH₃ CH(CH₃)C≡CH B.868 H CF₃ CH(CH₃)C≡CH B.869 H Cl CH(CH₃)C≡CH B.870 H OCH₃ CH(CH₃)C≡CH B.871 CH₂CH₃ CH₃ CH(CH₃)C≡CH B.872 CH₂CH₃ CH₂CH₃ CH(CH₃)C≡CH B.873 CH₂CH₃ CF₃ CH(CH₃)C≡CH B.874 CH₂CH₃ Cl CH(CH₃)C≡CH B.875 CH₂CH₃ OCH₃ CH(CH₃)C≡CH B.876 CHF₂ CH₃ CH(CH₃)C≡CH B.877 CHF₂ CH₂CH₃ CH(CH₃)C≡CH B.878 CHF₂ CF₃ CH(CH₃)C≡CH B.879 CHF₂ Cl CH(CH₃)C≡CH B.880 CHF₂ OCH₃ CH(CH₃)C≡CH B.881 CH₂F CH₃ CH(CH₃)C≡CH B.882 CH₂F CH₂CH₃ CH(CH₃)C≡CH B.883 CH₂F CF₃ CH(CH₃)C≡CH B.884 CH₂F Cl CH(CH₃)C≡CH B.885 CH₂F OCH₃ CH(CH₃)C≡CH B.886 OCH₃ CH₃ CH(CH₃)C≡CH B.887 OCH₃ CH₂CH₃ CH(CH₃)C≡CH B.888 OCH₃ CF₃ CH(CH₃)C≡CH B.889 OCH₃ Cl CH(CH₃)C≡CH B.890 OCH₃ OCH₃ CH(CH₃)C≡CH B.891 OCH₂CH₃ CH₃ CH(CH₃)C≡CH B.892 OCH₂CH₃ CH₂CH₃ CH(CH₃)C≡CH B.893 OCH₂CH₃ CF₃ CH(CH₃)C≡CH B.894 OCH₂CH₃ Cl CH(CH₃)C≡CH B.895 OCH₂CH₃ OCH₃ CH(CH₃)C≡CH B.896 CN CH₃ CH(CH₃)C≡CH B.897 CN CH₂CH₃ CH(CH₃)C≡CH B.898 CN CF₃ CH(CH₃)C≡CH B.899 CN Cl CH(CH₃)C≡CH B.900 CN OCH₃ CH(CH₃)C≡CH B.901 H CH₃ CH₂CH₂—O—CH₂CH₃ B.902 H CH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.903 H CF₃ CH₂CH₂—O—CH₂CH₃ B.904 H Cl CH₂CH₂—O—CH₂CH₃ B.905 H OCH₃ CH₂CH₂—O—CH₂CH₃ B.906 CH₂CH₃ CH₃ CH₂CH₂—O—CH₂CH₃ B.907 CH₂CH₃ CH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.908 CH₂CH₃ CF₃ CH₂CH₂—O—CH₂CH₃ B.909 CH₂CH₃ Cl CH₂CH₂—O—CH₂CH₃ B.910 CH₂CH₃ OCH₃ CH₂CH₂—O—CH₂CH₃ B.911 CHF₂ CH₃ CH₂CH₂—O—CH₂CH₃ B.912 CHF₂ CH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.913 CHF₂ CF₃ CH₂CH₂—O—CH₂CH₃ B.914 CHF₂ Cl CH₂CH₂—O—CH₂CH₃ B.915 CHF₂ OCH₃ CH₂CH₂—O—CH₂CH₃ B.916 CH₂F CH₃ CH₂CH₂—O—CH₂CH₃ B.917 CH₂F CH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.918 CH₂F CF₃ CH₂CH₂—O—CH₂CH₃ B.919 CH₂F Cl CH₂CH₂—O—CH₂CH₃ B.920 CH₂F OCH₃ CH₂CH₂—O—CH₂CH₃ B.921 OCH₃ CH₃ CH₂CH₂—O—CH₂CH₃ B.922 OCH₃ CH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.923 OCH₃ CF₃ CH₂CH₂—O—CH₂CH₃ B.924 OCH₃ Cl CH₂CH₂—O—CH₂CH₃ B.925 OCH₃ OCH₃ CH₂CH₂—O—CH₂CH₃ B.926 OCH₂CH₃ CH₃ CH₂CH₂—O—CH₂CH₃ B.927 OCH₂CH₃ CH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.928 OCH₂CH₃ CF₃ CH₂CH₂—O—CH₂CH₃ B.929 OCH₂CH₃ Cl CH₂CH₂—O—CH₂CH₃ B.930 OCH₂CH₃ OCH₃ CH₂CH₂—O—CH₂CH₃ B.931 CN CH₃ CH₂CH₂—O—CH₂CH₃ B.932 CN CH₂CH₃ CH₂CH₂—O—CH₂CH₃ B.933 CN CF₃ CH₂CH₂—O—CH₂CH₃ B.934 CN Cl CH₂CH₂—O—CH₂CH₃ B.935 CN OCH₃ CH₂CH₂—O—CH₂CH₃ B.936 H CH₃ CH₂—C₆H₅ B.937 H CH₂CH₃ CH₂—C₆H₅ B.938 H CF₃ CH₂—C₆H₅ B.939 H Cl CH₂—C₆H₅ B.940 H OCH₃ CH₂—C₆H₅ B.941 CH₂CH₃ CH₃ CH₂—C₆H₅ B.942 CH₂CH₃ CH₂CH₃ CH₂—C₆H₅ B.943 CH₂CH₃ CF₃ CH₂—C₆H₅ B.944 CH₂CH₃ Cl CH₂—C₆H₅ B.945 CH₂CH₃ OCH₃ CH₂—C₆H₅ B.946 CHF₂ CH₃ CH₂—C₆H₅ B.947 CHF₂ CH₂CH₃ CH₂—C₆H₅ B.948 CHF₂ CF₃ CH₂—C₆H₅ B.949 CHF₂ Cl CH₂—C₆H₅ B.950 CHF₂ OCH₃ CH₂—C₆H₅ B.951 CH₂F CH₃ CH₂—C₆H₅ B.952 CH₂F CH₂CH₃ CH₂—C₆H₅ B.953 CH₂F CF₃ CH₂—C₆H₅ B.954 CH₂F Cl CH₂—C₆H₅ B.955 CH₂F OCH₃ CH₂—C₆H₅ B.956 OCH₃ CH₃ CH₂—C₆H₅ B.957 OCH₃ CH₂CH₃ CH₂—C₆H₅ B.958 OCH₃ CF₃ CH₂—C₆H₅ B.959 OCH₃ Cl CH₂—C₆H₅ B.960 OCH₃ OCH₃ CH₂—C₆H₅ B.961 OCH₂CH₃ CH₃ CH₂—C₆H₅ B.962 OCH₂CH₃ CH₂CH₃ CH₂—C₆H₅ B.963 OCH₂CH₃ CF₃ CH₂—C₆H₅ B.964 OCH₂CH₃ Cl CH₂—C₆H₅ B.965 OCH₂CH₃ OCH₃ CH₂—C₆H₅ B.966 CN CH₃ CH₂—C₆H₅ B.967 CN CH₂CH₃ CH₂—C₆H₅ B.968 CN CF₃ CH₂—C₆H₅ B.969 CN Cl CH₂—C₆H₅ B.970 CN OCH₃ CH₂—C₆H₅ B.971 H CH₃ cyclopropyl B.972 H CH₂CH₃ cyclopropyl B.973 H CF₃ cyclopropyl B.974 H Cl cyclopropyl B.975 H OCH₃ cyclopropyl B.976 CH₂CH₃ CH₃ cyclopropyl B.977 CH₂CH₃ CH₂CH₃ cyclopropyl B.978 CH₂CH₃ CF₃ cyclopropyl B.979 CH₂CH₃ Cl cyclopropyl B.980 CH₂CH₃ OCH₃ cyclopropyl B.981 CHF₂ CH₃ cyclopropyl B.982 CHF₂ CH₂CH₃ cyclopropyl B.983 CHF₂ CF₃ cyclopropyl B.984 CHF₂ Cl cyclopropyl B.985 CHF₂ OCH₃ cyclopropyl B.986 CH₂F CH₃ cyclopropyl B.987 CH₂F CH₂CH₃ cyclopropyl B.988 CH₂F CF₃ cyclopropyl B.989 CH₂F Cl cyclopropyl B.990 CH₂F OCH₃ cyclopropyl B.991 OCH₃ CH₃ cyclopropyl B.992 OCH₃ CH₂CH₃ cyclopropyl B.993 OCH₃ CF₃ cyclopropyl B.994 OCH₃ Cl cyclopropyl B.995 OCH₃ OCH₃ cyclopropyl B.996 OCH₂CH₃ CH₃ cyclopropyl B.997 OCH₂CH₃ CH₂CH₃ cyclopropyl B.998 OCH₂CH₃ CF₃ cyclopropyl B.999 OCH₂CH₃ Cl cyclopropyl B.1000 OCH₂CH₃ OCH₃ cyclopropyl B.1001 CN CH₃ cyclopropyl B.1002 CN CH₂CH₃ cyclopropyl B.1003 CN CF₃ cyclopropyl B.1004 CN Cl cyclopropyl B.1005 CN OCH₃ cyclopropyl B.1006 H CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1007 H CH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1008 H CF₃ CH₂-(2,2-Cl₂-cyciopropyl) B.1009 H Cl CH₂-(2,2-Cl₂-cyclopropyl) B.1010 H OCH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1011 CH₂CH₃ CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1012 CH₂CH₃ CH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1013 CH₂CH₃ CF₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1014 CH₂CH₃ Cl CH₂-(2,2-Cl₂-cyclopropyl) B.1015 CH₂CH₃ OCH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1016 CHF₂ CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1017 CHF₂ CH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1018 CHF₂ CF₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1019 CHF₂ Cl CH₂-(2,2-Cl₂-cyclopropyl) B.1020 CHF₂ OCH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1021 CH₂F CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1022 CH₂F CH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1023 CH₂F CF₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1024 CH₂F Cl CH₂-(2,2-Cl₂-cyclopropyl) B.1025 CH₂F OCH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1026 OCH₃ CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B 1027 OCH₃ CH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1028 CCH₃ CF₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1029 OCH₃ Cl CH₂-(2,2-Cl₂-cyclopropyl) B.1030 OCH₃ OCH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1031 OCH₂CH₃ CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1032 OCH₂CH₃ CH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.1033 OCH₂CH₃ CF₃ CH₂-(2,2-Cl₂-cyclopropyl) B.2067 OCH₂CH₃ Cl CH₂-(2,2-Cl₂-cyclopropyl) B.2068 OCH₂CH₃ OCH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.2069 CN CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.2070 CN CH₂CH₃ CH₂-(2,2-Cl₂-cyclopropyl) B.2071 CN CF₃ CH₂-(2,2-Cl₂-cyclopropyl) B.2072 CN Cl CH₂-(2,2-Cl₂-cyclopropyl) B.2073 CN OCH₃ CH₂-(2,2-Cl₂-cyclopropyl)

TABLE C No. R¹ R^(x) R^(y) R^(z) C.1 CH₃ H H H C.2 CH₃ H CH₃ H C.3 CH₃ H C₂H₅ H C.4 CH₃ H C₃H₇ H C.5 CH₃ H C₄H₉ H C.6 CH₃ H CH(CH₃)₂ H C.7 CH₃ H cyclopropyl H C.8 CH₃ H CF₃ H C.9 CH₃ H OCH₃ H C.10 CH₃ H OC₂H₅ H C.11 CH₃ H CH₂—C₆H₅ H C.12 CH₃ H CH(CH₃)C₆H₅ H C.13 CH₃ H C₆H₅ H C.14 CH₃ H 4-F—C₆H₅ H C.15 CH₃ H 4-Cl-2-pyridyl H C.16 CH₃ H F H C.17 CH₃ H CN H C.18 CH₃ CH₃ H H C.19 CH₃ CH₃ CH₃ H C.20 CH₃ CH₃ C₂H₅ H C.21 CH₃ CH₃ C₃H₇ H C.22 CH₃ CH₃ C₄H₉ H C.23 CH₃ CH₃ CH(CH₃)₂ H C.24 CH₃ CH₃ cyclopropyl H C.25 CH₃ CH₃ CF₃ H C.26 CH₃ CH₃ OCH₃ H C.27 CH₃ CH₃ OC₂H₅ H C.28 CH₃ CH₃ CH₂—C₆H₅ H C.29 CH₃ CH₃ CH(CH₃)C₆H₅ H C.30 CH₃ CH₃ C₆H₅ H C.31 CH₃ CH₃ 4-F—C₆H₅ H C.32 CH₃ CH₃ 4-Cl-2-pyridyl H C.33 CH₃ CH₃ F H C.34 CH₃ CH₃ CN H C.35 CH₃ C₂H₅ H H C.36 CH₃ C₂H₅ CH₃ H C.37 CH₃ C₂H₅ C₂H₅ H C.38 CH₃ C₂H₅ C₃H₇ H C.39 CH₃ C₂H₅ C₄H₉ H C.40 CH₃ C₂H₅ CH(CH₃)₂ H C.41 CH₃ C₂H₅ cyclopropyl H C.42 CH₃ C₂H₅ CF₃ H C.43 CH₃ C₂H₅ OCH₃ H C.44 CH₃ C₂H₅ OC₂H₅ H C.45 CH₃ C₂H₅ CH₂—C₆H₅ H C.46 CH₃ C₂H₅ CH(CH₃)C₆H₅ H C.47 CH₃ C₂H₅ C₆H₅ H C.48 CH₃ C₂H₅ 4-F—C₆H₅ H C.49 CH₃ C₂H₅ 4-Cl-2-pyridyl H C.50 CH₃ C₂H₅ F H C.51 CH₃ C₂H₅ CN H C.52 CH₃ cyclopropyl H H C.53 CH₃ cyclopropyl CH₃ H C.54 CH₃ cyclopropyl C₂H₅ H C.55 CH₃ cyclopropyl C₃H₇ H C.56 CH₃ cyclopropyl C₄H₉ H C.57 CH₃ cyclopropyl CH(CH₃)₂ H C.58 CH₃ cyclopropyl cyclopropyl H C.59 CH₃ cyclopropyl CF₃ H C.60 CH₃ cyclopropyl OCH₃ H C.61 CH₃ cyclopropyl OC₂H₅ H C.62 CH₃ cyclopropyl CH₂—C₆H₅ H C.63 CH₃ cyclopropyl CH(CH₃)C₆H₅ H C.64 CH₃ cyclopropyl C₆H₅ H C.65 CH₃ cyclopropyl 4-F—C₆H₅ H C.66 CH₃ cyclopropyl 4-Cl-2-pyridyl H C.67 CH₃ cyclopropyl F H C.68 CH₃ cyclopropyl CN H C.69 CH₃ CF₃ H H C.70 CH₃ CF₃ CH₃ H C.71 CH₃ CF₃ C₂H₅ H C.72 CH₃ CF₃ C₃H₇ H C.73 CH₃ CF₃ C₄H₉ H C.74 CH₃ CF₃ CH(CH₃)₂ H C.75 CH₃ CF₃ cyclopropyl H C.76 CH₃ CF₃ CF₃ H C.77 CH₃ CF₃ OCH₃ H C.78 CH₃ CF₃ OC₂H₅ H C.79 CH₃ CF₃ CH₂—C₆H₅ H C.80 CH₃ CF₃ CH(CH₃)C₆H₅ H C.81 CH₃ CF₃ C₆H₅ H C.82 CH₃ CF₃ 4-F—C₆H₅ H C.83 CH₃ CF₃ 4-Cl-2-pyridyl H C.84 CH₃ CF₃ F H C.85 CH₃ CF₃ CN H C.86 CH₃ Cl H H C.87 CH₃ Cl CH₃ H C.88 CH₃ C1 C₂H₅ H C.89 CH₃ Cl C₃H₇ H C.90 CH₃ Cl C₄H₉ H C.91 CH₃ Cl CH(CH₃)2 H C.92 CH₃ Cl cyclopropyl H C.93 CH₃ Cl CF₃ H C.94 CH₃ Cl OCH₃ H C.95 CH₃ Cl OC₂H₅ H C.96 CH₃ Cl CH₂—C₆H₅ H C.97 CH₃ Cl CH(CH₃)C₆H₅ H C.98 CH₃ Cl C₆H₅ H C.99 CH₃ Cl 4-F—C₆H₅ H C.100 CH₃ Cl 4-Cl-2-pyridyl H C.101 CH₃ Cl F H C.102 CH₃ Cl CN H C.103 CH₃ F H H C.104 CH₃ F CH₃ H C.105 CH₃ F C₂H₅ H C.106 CH₃ F C₃H₇ H C.107 CH₃ F C₄H₉ H C.108 CH₃ F CH(CH₃)₂ H C.109 CH₃ F cyclopropyl H C.110 CH₃ F CF₃ H C.111 CH₃ F OCH₃ H C.112 CH₃ F OC₂H₅ H C.113 CH₃ F CH₂—C₆H₅ H C.114 CH₃ F CH(CH₃)C₆H₅ H C.115 CH₃ F C₆H₅ H C.116 CH₃ F 4-F—C₆H₅ H C.117 CH₃ F 4-Cl-2-pyridyl H C.118 CH₃ F F H C.119 CH₃ F CN H C.120 CH₃ OCH₃ H H C.121 CH₃ OCH₃ CH₃ H C.122 CH₃ OCH₃ C₂H₅ H C.123 CH₃ OCH₃ C₃H₇ H C.124 CH₃ OCH₃ C₄H₉ H C.125 CH₃ OCH₃ CH(CH₃)2 H C.126 CH₃ OCH₃ cyclopropyl H C.127 CH₃ OCH₃ CF₃ H C.128 CH₃ OCH₃ OCH₃ H C.129 CH₃ OCH₃ OC₂H₅ H C.130 CH₃ OCH₃ CH₂—C₆H₅ H C.131 CH₃ OCH₃ CH(CH₃)C₆H₅ H C.132 CH₃ OCH₃ C₆H₅ H C.133 CH₃ OCH₃ 4-F—C₆H₅ H C.134 CH₃ OCH₃ 4-Cl-2-pyridyl H C.135 CH₃ OCH₃ F H C.136 CH₃ OCH₃ CN H C.137 CH₃ H H CH₃ C.138 CH₃ H CH₃ CH₃ C.139 CH₃ H C₂H₅ CH₃ C.140 CH₃ H C₃H₇ CH₃ C.141 CH₃ H C₄H₉ CH₃ C.142 CH₃ H CH(CH₃)2 CH₃ C.143 CH₃ H cyclopropyl CH₃ C.144 CH₃ H CF₃ CH₃ C.145 CH₃ H OCH₃ CH₃ C.146 CH₃ H OC₂H₅ CH₃ C.147 CH₃ H CH₂—C₆H₅ CH₃ C.148 CH₃ H CH(CH₃)C₆H₅ CH₃ C.149 CH₃ H C₆H₅ CH₃ C.150 CH₃ H 4-F—C₆H₅ CH₃ C.151 CH₃ H 4-Cl-2-pyridyl CH₃ C.152 CH₃ H F CH₃ C.153 CH₃ H CN CH₃ C.154 CH₃ CH₃ H CH₃ C.155 CH₃ CH₃ CH₃ CH₃ C.156 CH₃ CH₃ C₂H₅ CH₃ C.157 CH₃ CH₃ C₃H₇ CH₃ C.158 CH₃ CH₃ C₄H₉ CH₃ C.159 CH₃ CH₃ CH(CH₃)₂ CH₃ C.160 CH₃ CH₃ cyclopropyl CH₃ C.161 CH₃ CH₃ CF₃ CH₃ C.162 CH₃ CH₃ OCH₃ CH₃ C.163 CH₃ CH₃ OC₂H₅ CH₃ C.164 CH₃ CH₃ CH₂—C₆H₅ CH₃ C.165 CH₃ CH₃ CH(CH₃)C₆H₅ CH₃ C.166 CH₃ CH₃ C₆H₅ CH₃ C.167 CH₃ CH₃ 4-F—C₆H₅ CH₃ C.168 CH₃ CH₃ 4-Cl-2-pyridyl CH₃ C.169 CH₃ CH₃ F CH₃ C.170 CH₃ CH₃ CN CH₃ C.171 CH₃ C₂H₅ H CH₃ C.172 CH₃ C₂H₅ CH₃ CH₃ C.173 CH₃ C₂H₅ C₂H₅ CH₃ C.174 CH₃ C₂H₅ C₃H₇ CH₃ C.175 CH₃ C₂H₅ C₄H₉ CH₃ C.176 CH₃ C₂H₅ CH(CH₃)₂ CH₃ C.177 CH₃ C₂H₅ cyclopropyl CH₃ C.178 CH₃ C₂H₅ CF₃ CH₃ C.179 CH₃ C₂H₅ OCH₃ CH₃ C.180 CH₃ C₂H₅ OC₂H₅ CH₃ C.181 CH₃ C₂H₅ CH₂—C₆H₅ CH₃ C.182 CH₃ C₂H₅ CH(CH₃)C₆H₅ CH₃ C.183 CH₃ C₂H₅ C₆H₅ CH₃ C.184 CH₃ C₂H₅ 4-F—C₆H₅ CH₃ C.185 CH₃ C₂H₅ 4-Cl-2-pyridyl CH₃ C.186 CH₃ C₂H₅ F CH₃ C.187 CH₃ C₂H₅ CN CH₃ C.188 CH₃ cyclopropyl H CH₃ C.189 CH₃ cyclopropyl CH₃ CH₃ C.190 CH₃ cyclopropyl C₂H₅ CH₃ C.191 CH₃ cyclopropyl C₃H₇ CH₃ C.192 CH₃ cyclopropyl C₄H₉ CH₃ C.193 CH₃ cyclopropyl CH(CH₃)₂ CH₃ C.194 CH₃ cyclopropyl cyclopropyl CH₃ C.195 CH₃ cyclopropyl CF₃ CH₃ C.196 CH₃ cyclopropyl OCH₃ CH₃ C.197 CH₃ cyclopropyl OC₂H₅ CH₃ C.198 CH₃ cyclopropyl CH₂—C₆H₅ CH₃ C.199 CH₃ cyclopropyl CH(CH₃)C₆H₅ CH₃ C.200 CH₃ cyclopropyl C₆H₅ CH₃ C.201 CH₃ cyclopropyl 4-F—C₆H₅ CH₃ C.202 CH₃ cyclopropyl 4-Cl-2-pyridyl CH₃ C.203 CH₃ cyclopropyl F CH₃ C.204 CH₃ cyclopropyl CN CH₃ C.205 CH₃ CF₃ H CH₃ C.206 CH₃ CF₃ CH₃ CH₃ C.207 CH₃ CF₃ C₂H₅ CH₃ C.208 CH₃ CF₃ C₃H₇ CH₃ C.209 CH₃ CF₃ C₄H₉ CH₃ C.210 CH₃ CF₃ CH(CH₃)₂ CH₃ C.211 CH₃ CF₃ cyclopropyl CH₃ C.212 CH₃ CF₃ CF₃ CH₃ C.213 CH₃ CF₃ OCH₃ CH₃ C.214 CH₃ CF₃ OC₂H₅ CH₃ C.215 CH₃ CF₃ CH₂—C₆H₅ CH₃ C.216 CH₃ CF₃ CH(CH₃)C₆H₅ CH₃ C.217 CH₃ CF₃ C₆H₅ CH₃ C.218 CH₃ CF₃ 4-F—C₆H₅ CH₃ C.219 CH₃ CF₃ 4-Cl-2-pyridyl CH₃ C.220 CH₃ CF₃ F CH₃ C.221 CH₃ CF₃ CN CH₃ C.222 CH₃ Cl H CH₃ C.223 CH₃ Cl CH₃ CH₃ C.224 CH₃ CI C₂H₅ CH₃ C.225 CH₃ Cl C₃H₇ CH₃ C.226 CH₃ Cl C₄H₉ CH₃ C.227 CH₃ Cl CH(CH₃)₂ CH₃ C.228 CH₃ Cl cyclopropyl CH₃ C.229 CH₃ Cl CF₃ CH₃ C.230 CH₃ Cl OCH₃ CH₃ C.231 CH₃ Cl OC₂H₅ CH₃ C.232 CH₃ Cl CH₂—C₆H₅ CH₃ C.233 CH₃ Cl CH(CH₃)C₆H₅ CH₃ C.234 CH₃ Cl C₆H₅ CH₃ C.235 CH₃ Cl 4-F—C₆H₅ CH₃ C.236 CH₃ Cl 4-Cl-2-pyridyl CH₃ C.237 CH₃ CI F CH₃ C.238 CH₃ Cl CN CH₃ C.239 CH₃ F H CH₃ C.240 CH₃ F CH₃ CH₃ C.241 CH₃ F C₂H₅ CH₃ C.242 CH₃ F C₃H₇ CH₃ C.243 CH₃ F C₄H₉ CH₃ C.244 CH₃ F CH(CH₃)₂ CH₃ C.245 CH₃ F cyclopropyl CH₃ C.246 CH₃ F CF₃ CH₃ C.247 CH₃ F OCH₃ CH₃ C.248 CH₃ F OC₂H₅ CH₃ C.249 CH₃ F CH₂—C₆H₅ CH₃ C.250 CH₃ F CH(CH₃)C₆H₅ CH₃ C.251 CH₃ F C₆H₅ CH₃ C.252 CH₃ F 4-F—C₆H₅ CH₃ C.253 CH₃ F 4-Cl-2-pyridyl CH₃ C.254 CH₃ F F CH₃ C.255 CH₃ F CN CH₃ C.256 CH₃ OCH₃ H CH₃ C.257 CH₃ OCH₃ CH₃ CH₃ C.258 CH₃ OCH₃ C₂H₅ CH₃ C.259 CH₃ OCH₃ C₃H₇ CH₃ C.260 CH₃ OCH₃ C₄H₉ CH₃ C.261 CH₃ OCH₃ CH(CH₃)₂ CH₃ C.262 CH₃ OCH₃ cyclopropyl CH₃ C.263 CH₃ OCH₃ CF₃ CH₃ C.264 CH₃ OCH₃ OCH₃ CH₃ C.265 CH₃ OCH₃ OC₂H₅ CH₃ C.266 CH₃ OCH₃ CH₂—C₆H₅ CH₃ C.267 CH₃ OCH₃ CH(CH₃)C₆H₅ CH₃ C.268 CH₃ OCH₃ C₆H₅ CH₃ C.269 CH₃ OCH₃ 4-F—C₆H₅ CH₃ C.270 CH₃ OCH₃ 4-Cl-2-pyridyl CH₃ C.271 CH₃ OCH₃ F CH₃ C.272 CH₃ OCH₃ CN CH₃ C.273 H CH₃ H H C.274 H CH₃ CH₃ H C.275 H CH₃ C₂H₅ H C.276 H CH₃ C₃H₇ H C.277 H CH₃ C₄H₉ H C.278 H CH₃ CH(CH₃)₂ H C.279 H CH₃ cyclopropyl H C.280 H CH₃ CF₃ H C.281 H CH₃ OCH₃ H C.282 H CH₃ OC₂H₅ H C.283 H CH₃ CH₂—C₆H₅ H C.284 H CH₃ CH(CH₃)C₆H₅ H C.285 H CH₃ C₆H₅ H C.286 H CH₃ 4-F—C₆H₅ H C.287 H CH₃ 4-Cl-2-pyridyl H C.288 H CH₃ F H C.289 H CH₃ CN H C.290 H CH₃ H CH₃ C.291 H CH₃ CH₃ CH₃ C.292 H CH₃ C₂H₅ CH₃ C.293 H CH₃ C₃H₇ CH₃ C.294 H CH₃ C₄H₉ CH₃ C.295 H CH₃ CH(CH₃)₂ CH₃ C.296 H CH₃ cyclopropyl CH₃ C.297 H CH₃ CF₃ CH₃ C.298 H CH₃ OCH₃ CH₃ C.299 H CH₃ OC₂H₅ CH₃ C.300 H CH₃ CH₂—C₆H₅ CH₃ C.301 H CH₃ CH(CH₃)C₆H₅ CH₃ C.302 H CH₃ C₆H₅ CH₃ C.303 H CH₃ 4-F—C₆H₅ CH₃ C.304 H CH₃ 4-Cl-2-pyridyl CH₃ C.305 H CH₃ F CH₃ C.306 H CH₃ CN CH₃ C.307 H CF₃ H H C.308 H CF₃ CH₃ H C.309 H CF₃ C₂H₅ H C.310 H CF₃ C₃H₇ H C.311 H CF₃ C₄H₉ H C.312 H CF₃ CH(CH₃)₂ H C.313 H CF₃ cyclopropyl H C.314 H CF₃ CF₃ H C.315 H CF₃ OCH₃ H C.316 H CF₃ OC₂H₅ H C.317 H CF₃ CH₂—C₆H₅ H C.318 H CF₃ CH(CH₃)C₆H₅ H C.319 H CF₃ C₆H₅ H C.320 H CF₃ 4-F—C₆H₅ H C.321 H CF₃ 4-Cl-2-pyridyl H C.322 H CF₃ F H C.323 H CF₃ CN H C.324 H CF₃ H CH₃ C.325 H CF₃ CH₃ CH₃ C.326 H CF₃ C₂H₅ CH₃ C.327 H CF₃ C₃H₇ CH₃ C.328 H CF₃ C₄H₉ CH₃ C.329 H CF₃ CH(CH₃)₂ CH₃ C.330 H CF₃ cyclopropyl CH₃ C.331 H CF₃ CF₃ CH₃ C.332 H CF₃ OCH₃ CH₃ C.333 H CF₃ OC₂H₅ CH₃ C.334 H CF₃ CH₂—C₆H₅ CH₃ C.335 H CF₃ CH(CH₃)C₆H₅ CH₃ C.336 H CF₃ C₆H₅ CH₃ C.337 H CF₃ 4-F—C₆H₅ CH₃ C.338 H CF₃ 4-Cl-2-pyridyl CH₃ C.339 H CF₃ F CH₃ C.340 H CF₃ CN CH₃ C.341 CF₃ CH₃ H H C.342 CF₃ CH₃ CH₃ H C.343 CF₃ CH₃ C₂H₅ H C.344 CF₃ CH₃ C₃H₇ H C.345 CF₃ CH₃ C₄H₉ H C.346 CF₃ CH₃ CH(CH₃)₂ H C.347 CF₃ CH₃ cyclopropyl H C.348 CF₃ CH₃ CF₃ H C.349 CF₃ CH₃ OCH₃ H C.350 CF₃ CH₃ OC₂H₅ H C.351 CF₃ CH₃ CH₂—C₆H₅ H C.352 CF₃ CH₃ CH(CH₃)C₆H₅ H C.353 CF₃ CH₃ C₆H₅ H C.354 CF₃ CH₃ 4-F—C₆H₅ H C.355 CF₃ CH₃ 4-Cl-2-pyridyl H C.356 CF₃ CH₃ F H C.357 CF₃ CH₃ CN H C.358 CF₃ CH₃ H CH₃ C.359 CF₃ CH₃ CH₃ CH₃ C.360 CF₃ CH₃ C₂H₅ CH₃ C.361 CF₃ CH₃ C₃H₇ CH₃ C.362 CF₃ CH₃ C₄H₉ CH₃ C.363 CF₃ CH₃ CH(CH₃)₂ CH₃ C.364 CF₃ CH₃ cyclopropyl CH₃ C.365 CF₃ CH₃ CF₃ CH₃ C.366 CF₃ CH₃ OCH₃ CH₃ C.367 CF₃ CH₃ OC₂H₅ CH₃ C.368 CF₃ CH₃ CH₂—C₆H₅ CH₃ C.369 CF₃ CH₃ CH(CH₃)C₆H₅ CH₃ C.370 CF₃ CH₃ C₆H₅ CH₃ C.371 CF₃ CH₃ 4-F—C₆H₅ CH₃ C.372 CF₃ CH₃ 4-Cl-2-pyridyl CH₃ C.373 CF₃ CH₃ F CH₃ C.374 CF₃ CH₃ CN CH₃ C.375 CF₃ CF₃ H H C.376 CF₃ CF₃ CH₃ H C.377 CF₃ CF₃ C₂H₅ H C.378 CF₃ CF₃ C₃H₇ H C.379 CF₃ CF₃ C₄H₉ H C.380 CF₃ CF₃ CH(CH₃)₂ H C.381 CF₃ CF₃ cyclopropyl H C.382 CF₃ CF₃ CF₃ H C.383 CF₃ CF₃ OCH₃ H C.384 CF₃ CF₃ OC₂H₅ H C.385 CF₃ CF₃ CH₂—C₆H₅ H C.386 CF₃ CF₃ CH(CH₃)C₆H₅ H C.387 CF₃ CF₃ C₆H₅ H C.388 CF₃ CF₃ 4-F—C₆H₅ H C.389 CF₃ CF₃ 4-Cl-2-pyridyl H C.390 CF₃ CF₃ F H C.391 CF₃ CF₃ CN H C.392 CF₃ CF₃ H CH₃ C.393 CF₃ CF₃ CH₃ CH₃ C.394 CF₃ CF₃ C₂H₅ CH₃ C.395 CF₃ CF₃ C₃H₇ CH₃ C.396 CF₃ CF₃ C₄H₉ CH₃ C.397 CF₃ CF₃ CH(CH₃)₂ CH₃ C.398 CF₃ CF₃ cyclopropyl CH₃ C.399 CF₃ CF₃ CF₃ CH₃ C.400 CF₃ CF₃ OCH₃ CH₃ C.401 CF₃ CF₃ OC₂H₅ CH₃ C.402 CF₃ CF₃ CH₂—C₆H₅ CH₃ C.403 CF₃ CF₃ CH(CH₃)C₆H₅ CH₃ C.404 CF₃ CF₃ C₆H₅ CH₃ C.405 CF₃ CF₃ 4-F—C₆H₅ CH₃ C.406 CF₃ CF₃ 4-Cl-2-pyridyl CH₃ C.407 CF₃ CF₃ F CH₃ C.408 CF₃ CF₃ CN CH₃ C.409 Cl CH₃ H H C.410 Cl CH₃ CH₃ H C.411 Cl CH₃ C₂H₅ H C.412 Cl CH₃ C₃H₇ H C.413 Cl CH₃ C₄H₉ H C.414 Cl CH₃ CH(CH₃)₂ H C.415 Cl CH₃ cyclopropyl H C.416 Cl CH₃ CF₃ H C.417 Cl CH₃ OCH₃ H C.418 Cl CH₃ OC₂H₅ H C.419 Cl CH₃ CH₂—C₆H₅ H C.420 Cl CH₃ CH(CH₃)C₆H₅ H C.421 Cl CH₃ C₆H₅ H C.422 Cl CH₃ 4-F—C₆H₅ H C.423 Cl CH₃ 4-Cl-2-pyridyl H C.424 Cl CH₃ F H C.425 Cl CH₃ CN H C.426 Cl CH₃ H CH₃ C.427 Cl CH₃ CH₃ CH₃ C.428 Cl CH₃ C₂H₅ CH₃ C.429 Cl CH₃ C₃H₇ CH₃ C.430 Cl CH₃ C₄H₉ CH₃ C.431 Cl CH₃ CH(CH₃)₂ CH₃ C.432 Cl CH₃ cyclopropyl CH₃ C.433 Cl CH₃ CF₃ CH₃ C.434 Cl CH₃ OCH₃ CH₃ C.435 Cl CH₃ OC₂H₅ CH₃ C.436 Cl CH₃ CH₂—C₆H₅ CH₃ C.437 Cl CH₃ CH(CH₃)C₆H₅ CH₃ C.438 Cl CH₃ C₆H₅ CH₃ C.439 Cl CH₃ 4-F—C₆H₅ CH₃ C.440 Cl CH₃ 4-Cl-2-pyridyl CH₃ C.441 Cl CH₃ F CH₃ C.442 Cl CH₃ CN CH₃ C.443 Cl CF₃ H H C.444 Cl CF₃ CH₃ H C.445 Cl CF₃ C₂H₅ H C.446 Cl CF₃ C₃H₇ H C.447 Cl CF₃ C₄H₉ H C.448 Cl CF₃ CH(CH₃)₂ H C.449 Cl CF₃ cyclopropyl H C.450 Cl CF₃ CF₃ H C.451 Cl CF₃ OCH₃ H C.452 Cl CF₃ OC₂H₅ H C.453 Cl CF₃ CH₂—C₆H₅ H C.454 Cl CF₃ CH(CH₃)C₆H₅ H C.455 Cl CF₃ C₆H₅ H C.456 Cl CF₃ 4-F—C₆H₅ H C.457 Cl CF₃ 4-Cl-2-pyridyl H C.458 Cl CF₃ F H C.459 Cl CF₃ CN H C.460 Cl CF₃ H CH₃ C.461 Cl CF₃ CH₃ CH₃ C.462 Cl CF₃ C₂H₅ CH₃ C.463 Cl CF₃ C₃H₇ CH₃ C.464 Cl CF₃ C₄H₉ CH₃ C.465 Cl CF₃ CH(CH₃)₂ CH₃ C.466 Cl CF₃ cyclopropyl CH₃ C.467 Cl CF₃ CF₃ CH₃ C.468 Cl CF₃ OCH₃ CH₃ C.469 Cl CF₃ OC₂H₅ CH₃ C.470 Cl CF₃ CH₂—C₆H₅ CH₃ C.471 Cl CF₃ CH(CH₃)C₆H₅ CH₃ C.472 Cl CF₃ C₆H₅ CH₃ C.473 Cl CF₃ 4-F—C₆H₅ CH₃ C.474 Cl CF₃ 4-Cl-2-pyridyl CH₃ C.475 Cl CF₃ F CH₃ C.476 Cl CF₃ CN CH₃ C.477 H CH₃ H F C.478 H CH₃ CH₃ F C.479 H CH₃ C₂H₅ F C.480 H CH₃ C₃H₇ F C.481 H CH₃ CH(CH₃)₂ F C.482 H CH₃ cyclopropyl F C.483 H CH₃ CF₃ F C.484 H CH₃ OCH₃ F C.485 H CH₃ C₆H₅ F C.486 H CH₃ 4-F—C₆H₅ F C.487 H CH₃ H C₂H₅ C.488 H CH₃ CH₃ C₂H₅ C.489 H CH₃ C₂H₅ C₂H₅ C.490 H CH₃ C₃H₇ C₂H₅ C.491 H CH₃ CH(CH₃)₂ C₂H₅ C.492 H CH₃ cyclopropyl C₂H₅ C.493 H CH₃ CF₃ C₂H₅ C.494 H CH₃ OCH₃ C₂H₅ C.495 H CH₃ C₆H₅ C₂H₅ C.496 H CH₃ 4-F—C₆H₅ C₂H₅ C.497 H CH₃ H CF₃ C.498 H CH₃ CH₃ CF₃ C.499 H CH₃ C₂H₅ CF₃ C.500 H CH₃ C₃H₇ CF₃ C.501 H CH₃ CH(CH₃)₂ CF₃ C.502 H CH₃ cyclopropyl CF₃ C.503 H CH₃ CF₃ CF₃ C.504 H CH₃ OCH₃ CF₃ C.505 H CH₃ C₆H₅ CF₃ C.506 H CH₃ 4-F—C₆H₅ CF₃ C.507 H CH₃ H CN C.508 H CH₃ CH₃ CN C.509 H CH₃ C₂H₅ CN C.510 H CH₃ C₃H₇ CN C.511 H CH₃ CH(CH₃)₂ CN C.512 H CH₃ cyclopropyl CN C.513 H CH₃ CF₃ CN C.514 H CH₃ OCH₃ CN C.515 H CH₃ C₆H₅ CN C.516 H CH₃ 4-F—C₆H₅ CN C.517 H CH₃ H Cl C.518 H CH₃ CH₃ Cl C.519 H CH₃ C₂H₅ Cl C.520 H CH₃ C₃H₇ Cl C.521 H CH₃ CH(CH₃)₂ Cl C.522 H CH₃ cyclopropyl Cl C.523 H CH₃ CF₃ Cl C.524 H CH₃ OCH₃ Cl C.525 H CH₃ C₆H₅ Cl C.526 H CH₃ 4-F—C₆H₅ Cl C.527 H CF₃ H F C.528 H CF₃ CH₃ F C.529 H CF₃ C₂H₅ F C.530 H CF₃ C₃H₇ F C.531 H CF₃ CH(CH₃)₂ F C.532 H CF₃ cyclopropyl F C.533 H CF₃ CF₃ F C.534 H CF₃ OCH₃ F C.535 H CF₃ C₆H₅ F C.536 H CF₃ 4-F—C₆H₅ F C.537 H CF₃ H C₂H₅ C.538 H CF₃ CH₃ C₂H₅ C.539 H CF₃ C₂H₅ C₂H₅ C.540 H CF₃ C₃H₇ C₂H₅ C.541 H CF₃ CH(CH₃)₂ C₂H₅ C.542 H CF₃ cyclopropyl C₂H₅ C.543 H CF₃ CF₃ C₂H₅ C.544 H CF₃ OCH₃ C₂H₅ C.545 H CF₃ C₆H₅ C₂H₅ C.546 H CF₃ 4-F—C₆H₅ C₂H₅ C.547 H CF₃ H CF₃ C.548 H CF₃ CH₃ CF₃ C.549 H CF₃ C₂H₅ CF₃ C.550 H CF₃ C₃H₇ CF₃ C.551 H CF₃ CH(CH₃)₂ CF₃ C.552 H CF₃ cyclopropyl CF₃ C.553 H CF₃ CF₃ CF₃ C.554 H CF₃ OCH₃ CF₃ C.555 H CF₃ C₆H₅ CF₃ C.556 H CF₃ 4-F—C₆H₅ CF₃ C.557 H CF₃ H CN C.558 H CF₃ CH₃ CN C.559 H CF₃ C₂H₅ CN C.560 H CF₃ C₃H₇ CN C.561 H CF₃ CH(CH₃)₂ CN C.562 H CF₃ cyclopropyl CN C.563 H CF₃ CF₃ CN C.564 H CF₃ OCH₃ CN C.565 H CF₃ C₆H₅ CN C.566 H CF₃ 4-F—C₆H₅ CN C.567 H CF₃ H Cl C.568 H CF₃ CH₃ Cl C.569 H CF₃ C₂H₅ Cl C.570 H CF₃ C₃H₇ Cl C.571 H CF₃ CH(CH₃)₂ Cl C.572 H CF₃ cyclopropyl Cl C.573 H CF₃ CF₃ Cl C.574 H CF₃ OCH₃ Cl C.575 H CF₃ C₆H₅ Cl C.576 H CF₃ 4-F—C₆H₅ Cl C.577 CF₃ CH₃ H F C.578 CF₃ CH₃ CH₃ F C.579 CF₃ CH₃ C₂H₅ F C.580 CF₃ CH₃ C₃H₇ F C.581 CF₃ CH₃ CH(CH₃)₂ F C.582 CF₃ CH₃ cyclopropyl F C.583 CF₃ CH₃ CF₃ F C.584 CF₃ CH₃ OCH₃ F C.585 CF₃ CH₃ C₆H₅ F C.586 CF₃ CH₃ 4-F—C₆H₅ F C.587 CF₃ CH₃ H C₂H₅ C.588 CF₃ CH₃ CH₃ C₂H₅ C.589 CF₃ CH₃ C₂H₅ C₂H₅ C.590 CF₃ CH₃ C₃H₇ C₂H₅ C.591 CF₃ CH₃ CH(CH₃)₂ C₂H₅ C.592 CF₃ CH₃ cyclopropyl C₂H₅ C.593 CF₃ CH₃ CF₃ C₂H₅ C.594 CF₃ CH₃ OCH₃ C₂H₅ C.595 CF₃ CH₃ C₆H₅ C₂H₅ C.596 CF₃ CH₃ 4-F—C₆H₅ C₂H₅ C.597 CF₃ CH₃ H CF₃ C.598 CF₃ CH₃ CH₃ CF₃ C.599 CF₃ CH₃ C₂H₅ CF₃ C.600 CF₃ CH₃ C₃H₇ CF₃ C.601 CF₃ CH₃ CH(CH₃)₂ CF₃ C.602 CF₃ CH₃ cyclopropyl CF₃ C.603 CF₃ CH₃ CF₃ CF₃ C.604 CF₃ CH₃ OCH₃ CF₃ C.605 CF₃ CH₃ C₆H₅ CF₃ C.606 CF₃ CH₃ 4-F—C₆H₅ CF₃ C.607 CF₃ CH₃ H CN C.608 CF₃ CH₃ CH₃ CN C.609 CF₃ CH₃ C₂H₅ CN C.610 CF₃ CH₃ C₃H₇ CN C.611 CF₃ CH₃ CH(CH₃)₂ CN C.612 CF₃ CH₃ cyclopropyl CN C.613 CF₃ CH₃ CF₃ CN C.614 CF₃ CH₃ OCH₃ CN C.615 CF₃ CH₃ C₆H₅ CN C.616 CF₃ CH₃ 4-F—C₆H₅ CN C.617 CF₃ CH₃ H Cl C.618 CF₃ CH₃ CH₃ Cl C.619 CF₃ CH₃ C₂H₅ Cl C.620 CF₃ CH₃ C₃H₇ Cl C.621 CF₃ CH₃ CH(CH₃)₂ Cl C.622 CF₃ CH₃ cyclopropyl Cl C.623 CF₃ CH₃ CF₃ Cl C.624 CF₃ CH₃ OCH₃ Cl C.625 CF₃ CH₃ C₆H₅ Cl C.626 CF₃ CH₃ 4-F—C₆H₅ Cl C.627 CF₃ CF₃ H F C.628 CF₃ CF₃ CH₃ F C.629 CF₃ CF₃ C₂H₅ F C.630 CF₃ CF₃ C₃H₇ F C.631 CF₃ CF₃ CH(CH₃)₂ F C.632 CF₃ CF₃ cyclopropyl F C.633 CF₃ CF₃ CF₃ F C.634 CF₃ CF₃ OCH₃ F C.635 CF₃ CF₃ C₆H₅ F C.636 CF₃ CF₃ 4-F—C₆H₅ F C.637 CF₃ CF₃ H C₂H₅ C.638 CF₃ CF₃ CH₃ C₂H₅ C.639 CF₃ CF₃ C₂H₅ C₂H₅ C.640 CF₃ CF₃ C₃H₇ C₂H₅ C.641 CF₃ CF₃ CH(CH₃)₂ C₂H₅ C.642 CF₃ CF₃ cyclopropyl C₂H₅ C.643 CF₃ CF₃ CF₃ C₂H₅ C.644 CF₃ CF₃ OCH₃ C₂H₅ C.645 CF₃ CF₃ C₆H₅ C₂H₅ C.646 CF₃ CF₃ 4-F—C₆H₅ C₂H₅ C.647 CF₃ CF₃ H CF₃ C.648 CF₃ CF₃ CH₃ CF₃ C.649 CF₃ CF₃ C₂H₅ CF₃ C.650 CF₃ CF₃ C₃H₇ CF₃ C.651 CF₃ CF₃ CH(CH₃)₂ CF₃ C.652 CF₃ CF₃ cyclopropyl CF₃ C.653 CF₃ CF₃ CF₃ CF₃ C.654 CF₃ CF₃ OCH₃ CF₃ C.655 CF₃ CF₃ C₆H₅ CF₃ C.656 CF₃ CF₃ 4-F—C₆H₅ CF₃ C.657 CF₃ CF₃ H CN C.658 CF₃ CF₃ CH₃ CN C.659 CF₃ CF₃ C₂H₅ CN C.660 CF₃ CF₃ C₃H₇ CN C.661 CF₃ CF₃ CH(CH₃)₂ CN C.662 CF₃ CF₃ cyclopropyl CN C.663 CF₃ CF₃ CF₃ CN C.664 CF₃ CF₃ OCH₃ CN C.665 CF₃ CF₃ C₆H₅ CN C.666 CF₃ CF₃ 4-F—C₆H₅ CN C.667 CF₃ CF₃ H Cl C.668 CF₃ CF₃ CH₃ Cl C.669 CF₃ CF₃ C₂H₅ Cl C.670 CF₃ CF₃ C₃H₇ Cl C.671 CF₃ CF₃ CH(CH₃)₂ Cl C.672 CF₃ CF₃ cyclopropyl Cl C.673 CF₃ CF₃ CF₃ Cl C.674 CF₃ CF₃ OCH₃ Cl C.675 CF₃ CF₃ C₆H₅ Cl C.676 CF₃ CF₃ 4-F—C₆H₅ Cl C.677 Cl CH₃ H F C.678 Cl CH₃ CH₃ F C.679 Cl CH₃ C₂H₅ F C.680 Cl CH₃ C₃H₇ F C.681 Cl CH₃ CH(CH₃)₂ F C.682 Cl CH₃ cyclopropyl F C.683 Cl CH₃ CF₃ F C.684 Cl CH₃ OCH₃ F C.685 Cl CH₃ C₆H₅ F C.686 Cl CH₃ 4-F—C₆H₅ F C.687 Cl CH₃ H C₂H₅ C.688 Cl CH₃ CH₃ C₂H₅ C.689 Cl CH₃ C₂H₅ C₂H₅ C.690 Cl CH₃ C₃H₇ C₂H₅ C.691 Cl CH₃ CH(CH₃)₂ C₂H₅ C.692 Cl CH₃ cyclopropyl C₂H₅ C.693 Cl CH₃ CF₃ C₂H₅ C.694 Cl CH₃ OCH₃ C₂H₅ C.695 Cl CH₃ C₆H₅ C₂H₅ C.696 Cl CH₃ 4-F—C₆H₅ C₂H₅ C.697 Cl CH₃ H CF₃ C.698 Cl CH₃ CH₃ CF₃ C.699 Cl CH₃ C₂H₅ CF₃ C.700 Cl CH₃ C₃H₇ CF₃ C.701 Cl CH₃ CH(CH₃)₂ CF₃ C.702 Cl CH₃ cyclopropyl CF₃ C.703 Cl CH₃ CF₃ CF₃ C.704 Cl CH₃ OCH₃ CF₃ C.705 Cl CH₃ C₆H₅ CF₃ C.706 Cl CH₃ 4-F—C₆H₅ CF₃ C.707 Cl CH₃ H CN C.708 Cl CH₃ CH₃ CN C.709 Cl CH₃ C₂H₅ CN C.710 Cl CH₃ C₃H₇ CN C.711 Cl CH₃ CH(CH₃)₂ CN C.712 Cl CH₃ cyclopropyl CN C.713 Cl CH₃ CF₃ CN C.714 Cl CH₃ OCH₃ CN C.715 Cl CH₃ C₆H₅ CN C.716 Cl CH₃ 4-F—C₆H₅ CN C.717 Cl CH₃ H Cl C.718 Cl CH₃ CH₃ Cl C.719 Cl CH₃ C₂H₅ Cl C.720 Cl CH₃ C₃H₇ Cl C.721 Cl CH₃ CH(CH₃)₂ Cl C.722 Cl CH₃ cyclopropyl Cl C.723 Cl CH₃ CF₃ Cl C.724 Cl CH₃ OCH₃ Cl C.725 Cl CH₃ C₆H₅ Cl C.726 Cl CH₃ 4-F—C₆H₅ Cl C.727 Cl CF₃ H F C.728 Cl CF₃ CH₃ F C.729 Cl CF₃ C₂H₅ F C.730 Cl CF₃ C₃H₇ F C.731 Cl CF₃ CH(CH₃)₂ F C.732 Cl CF₃ cyclopropyl F C.733 Cl CF₃ CF₃ F C.734 Cl CF₃ OCH₃ F C.735 Cl CF₃ C₆H₅ F C.736 Cl CF₃ 4-F—C₆H₅ F C.737 Cl CF₃ H C₂H₅ C.738 Cl CF₃ CH₃ C₂H₅ C.739 Cl CF₃ C₂H₅ C₂H₅ C.740 Cl CF₃ C₃H₇ C₂H₅ C.741 Cl CF₃ CH(CH₃)₂ C₂H₅ C.742 Cl CF₃ cyclopropyl C₂H₅ C.743 Cl CF₃ CF₃ C₂H₅ C.744 Cl CF₃ OCH₃ C₂H₅ C.745 Cl CF₃ C₆H₅ C₂H₅ C.746 Cl CF₃ 4-F—C₆H₅ C₂H₅ C.747 Cl CF₃ H CF₃ C.748 Cl CF₃ CH₃ CF₃ C.749 Cl CF₃ C₂H₅ CF₃ C.750 Cl CF₃ C₃H₇ CF₃ C.751 Cl CF₃ CH(CH₃)₂ CF₃ C.752 Cl CF₃ cyclopropyl CF₃ C.753 Cl CF₃ CF₃ CF₃ C.754 Cl CF₃ OCH₃ CF₃ C.755 Cl CF₃ C₆H₅ CF₃ C.756 Cl CF₃ 4-F—C₆H₅ CF₃ C.757 Cl CF₃ H CN C.758 Cl CF₃ CH₃ CN C.759 Cl CF₃ C₂H₅ CN C.760 Cl CF₃ C₃H₇ CN C.761 Cl CF₃ CH(CH₃)₂ CN C.762 Cl CF₃ cyclopropyl CN C.763 Cl CF₃ CF₃ CN C.764 Cl CF₃ OCH₃ CN C.765 Cl CF₃ C₆H₅ CN C.766 Cl CF₃ 4-F—C₆H₅ CN C.767 Cl CF₃ H Cl C.768 Cl CF₃ CH₃ Cl C.769 Cl CF₃ C₂H₅ Cl C.770 Cl CF₃ C₃H₇ Cl C.771 Cl CF₃ CH(CH₃)₂ Cl C.772 Cl CF₃ cyclopropyl Cl C.773 Cl CF₃ CF₃ Cl C.774 Cl CF₃ OCH₃ Cl C.775 Cl CF₃ C₆H₅ Cl C.776 Cl CF₃ 4-F—C₆H₅ Cl C.777 CH₃ H H F C.778 CH₃ H CH₃ F C.779 CH₃ H C₂H₅ F C.780 CH₃ H C₃H₇ F C.781 CH₃ H CH(CH₃)₂ F C.782 CH₃ H cyclopropyl F C.783 CH₃ H CF₃ F C.784 CH₃ H OCH₃ F C.785 CH₃ H C₆H₅ F C.786 CH₃ H 4-F—C₆H₅ F C.787 CH₃ CH₃ H F C.788 CH₃ CH₃ CH₃ F C.789 CH₃ CH₃ C₂H₅ F C.790 CH₃ CH₃ C₃H₇ F C.791 CH₃ CH₃ CH(CH₃)₂ F C.792 CH₃ CH₃ cyclopropyl F C.793 CH₃ CH₃ CF₃ F C.794 CH₃ CH₃ OCH₃ F C.795 CH₃ CH₃ C₆H₅ F C.796 CH₃ CH₃ 4-F—C₆H₅ F C.797 CH₃ C₂H₅ H F C.798 CH₃ C₂H₅ CH₃ F C.799 CH₃ C₂H₅ C₂H₅ F C.800 CH₃ C₂H₅ C₃H₇ F C.801 CH₃ C₂H₅ CH(CH₃)₂ F C.802 CH₃ C₂H₅ cyclopropyl F C.803 CH₃ C₂H₅ CF₃ F C.804 CH₃ C₂H₅ OCH₃ F C.805 CH₃ C₂H₅ C₆H₅ F C.806 CH₃ C₂H₅ 4-F—C₆H₅ F C.807 CH₃ cyclopropyl H F C.808 CH₃ cyclopropyl CH₃ F C.809 CH₃ cyclopropyl C₂H₅ F C.810 CH₃ cyclopropyl C₃H₇ F C.811 CH₃ cyclopropyl CH(CH₃)₂ F C.812 CH₃ cyclopropyl cyclopropyl F C.813 CH₃ cyclopropyl CF₃ F C.814 CH₃ cyclopropyl OCH₃ F C.815 CH₃ cyclopropyl C₆H₅ F C.816 CH₃ cyclopropyl 4-F—C₆H₅ F C.817 CH₃ CF₃ H F C.818 CH₃ CF₃ CH₃ F C.819 CH₃ CF₃ C₂H₅ F C.820 CH₃ CF₃ C₃H₇ F C.821 CH₃ CF₃ CH(CH₃)₂ F C.822 CH₃ CF₃ cyclopropyl F C.823 CH₃ CF₃ CF₃ F C.824 CH₃ CF₃ OCH₃ F C.825 CH₃ CF₃ C₆H₅ F C.826 CH₃ CF₃ 4-F—C₆H₅ F C.827 CH₃ Cl H F C.828 CH₃ Cl CH₃ F C.829 dH3 Cl C₂H₅ F C.830 CH₃ Cl C₃H₇ F C.831 CH₃ Cl CH(CH₃)₂ F C.832 CH₃ Cl cyclopropyl F C.833 CH₃ Cl CF₃ F C.834 CH₃ Cl OCH₃ F C.835 CH₃ Cl C₆H₅ F C.836 CH₃ Cl 4-F—C₆H₅ F C.837 CH₃ F H F C.838 CH₃ F CH₃ F C.839 CH₃ F C₂H₅ F C.840 CH₃ F C₃H₇ F C.841 CH₃ F CH(CH₃)₂ F C.842 CH₃ F cyclopropyl F C.843 CH₃ F CF₃ F C.844 CH₃ F OCH₃ F C.845 CH₃ F C₆H₅ F C.846 CH₃ F 4-F—C₆H₅ F C.847 CH₃ OCH₃ H F C.848 CH₃ OCH₃ CH₃ F C.849 CH₃ OCH₃ C₂H₅ F C.850 CH₃ OCH₃ C₃H₇ F C.851 CH₃ OCH₃ CH(CH₃)₂ F C.852 CH₃ OCH₃ cyclopropyl F C.853 CH₃ OCH₃ CF₃ F C.854 CH₃ OCH₃ OCH₃ F C.855 CH₃ OCH₃ C₆H₅ F C.856 CH₃ OCH₃ 4-F—C₆H₅ F C.857 CH₃ H H C₂H₅ C.858 CH₃ H CH₃ C₂H₅ C.859 CH₃ H C₂H₅ C₂H₅ C.860 CH₃ H C₃H₇ C₂H₅ C.861 CH₃ H CH(CH₃)₂ C₂H₅ C.862 CH₃ H cyclopropyl C₂H₅ C.863 CH₃ H CF₃ C₂H₅ C.864 CH₃ H OCH₃ C₂H₅ C.865 CH₃ H C₆H₅ C₂H₅ C.866 CH₃ H 4-F—C₆H₅ C₂H₅ C.867 CH₃ CH₃ H C₂H₅ C.868 CH₃ CH₃ CH₃ C₂H₅ C.869 CH₃ CH₃ C₂H₅ C₂H₅ C.870 CH₃ CH₃ C₃H₇ C₂H₅ C.871 CH₃ CH₃ CH(CH₃)₂ C₂H₅ C.872 CH₃ CH₃ cyclopropyl C₂H₅ C.873 CH₃ CH₃ CF₃ C₂H₅ C.874 CH₃ CH₃ OCH₃ C₂H₅ C.875 CH₃ CH₃ C₆H₅ C₂H₅ C.876 CH₃ CH₃ 4-F—C₆H₅ C₂H₅ C.877 CH₃ C₂H₅ H C₂H₅ C.878 CH₃ C₂H₅ CH₃ C₂H₅ C.879 CH₃ C₂H₅ C₂H₅ C₂H₅ C.880 CH₃ C₂H₅ C₃H₇ C₂H₅ C.881 CH₃ C₂H₅ CH(CH₃)₂ C₂H₅ C.882 CH₃ C₂H₅ cyclopropyl C₂H₅ C.883 CH₃ C₂H₅ CF₃ C₂H₅ C.884 CH₃ C₂H₅ OCH₃ C₂H₅ C.885 CH₃ C₂H₅ C₆H₅ C₂H₅ C.886 CH₃ C₂H₅ 4-F—C₆H₅ C₂H₅ C.887 CH₃ cyclopropyl H C₂H₅ C.888 CH₃ cyclopropyl CH₃ C₂H₅ C.889 CH₃ cyclopropyl C₂H₅ C₂H₅ C.890 CH₃ cyclopropyl C₃H₇ C₂H₅ C.891 CH₃ cyclopropyl CH(CH₃)₂ C₂H₅ C.892 CH₃ cyclopropyl cyclopropyl C₂H₅ C.893 CH₃ cyclopropyl CF₃ C₂H₅ C.894 CH₃ cyclopropyl OCH₃ C₂H₅ C.895 CH₃ cyclopropyl C₆H₅ C₂H₅ C.896 CH₃ cyclopropyl 4-F—C₆H₅ C₂H₅ C.897 CH₃ CF₃ H C₂H₅ C.898 CH₃ CF₃ CH₃ C₂H₅ C.899 CH₃ CF₃ C₂H₅ C₂H₅ C.900 CH₃ CF₃ C₃H₇ C₂H₅ C.901 CH₃ CF₃ CH(CH₃)₂ C₂H₅ C.902 CH₃ CF₃ cyclopropyl C₂H₅ C.903 CH₃ CF₃ CF₃ C₂H₅ C.904 CH₃ CF₃ OCH₃ C₂H₅ C.905 CH₃ CF₃ C₆H₅ C₂H₅ C.906 CH₃ CF₃ 4-F—C₆H₅ C₂H₅ C.907 CH₃ Cl H C₂H₅ C.908 CH₃ Cl CH₃ C₂H₅ C.909 CH₃ Cl C₂H₅ C₂H₅ C.910 CH₃ Cl C₃H₇ C₂H₅ C.911 CH₃ Cl CH(CH₃)₂ C₂H₅ C.912 CH₃ Cl cyclopropyl C₂H₅ C.913 CH₃ Cl CF₃ C₂H₅ C.914 CH₃ Cl OCH₃ C₂H₅ C.915 CH₃ Cl C₆H₅ C₂H₅ C.916 CH₃ Cl 4-F—C₆H₅ C₂H₅ C.917 CH₃ F H C₂H₅ C.918 CH₃ F CH₃ C₂H₅ C.919 CH₃ F C₂H₅ C₂H₅ C.920 CH₃ F C₃H₇ C₂H₅ C.921 CH₃ F CH(CH₃)₂ C₂H₅ C.922 CH₃ F cyclopropyl C₂H₅ C.923 CH₃ F CF₃ C₂H₅ C.924 CH₃ F OCH₃ C₂H₅ C.925 CH₃ F C₆H₅ C₂H₅ C.926 CH₃ F 4-F—C₆H₅ C₂H₅ C.927 CH₃ OCH₃ H C₂H₅ C.928 CH₃ OCH₃ CH₃ C₂H₅ C.929 CH₃ OCH₃ C₂H₅ C₂H₅ C.930 CH₃ OCH₃ C₃H₇ C₂H₅ C.931 CH₃ OCH₃ CH(CH₃)₂ C₂H₅ C.932 CH₃ OCH₃ cyclopropyl C₂H₅ C.933 CH₃ OCH₃ CF₃ C₂H₅ C.934 CH₃ OCH₃ OCH₃ C₂H₅ C.935 CH₃ OCH₃ C₆H₅ C₂H₅ C.936 CH₃ OCH₃ 4-F—C₆H₅ C₂H₅ C.937 CH₃ H H CF₃ C.938 CH₃ H CH₃ CF₃ C.939 CH₃ H C₂H₅ CF₃ C.940 CH₃ H C₃H₇ CF₃ C.941 CH₃ H CH(CH₃)₂ CF₃ C.942 CH₃ H cyclopropyl CF₃ C.943 CH₃ H CF₃ CF₃ C.944 CH₃ H OCH₃ CF₃ C.945 CH₃ H C₆H₅ CF₃ C.946 CH₃ H 4-F—C₆H₅ CF₃ C.947 CH₃ CH₃ H CF₃ C.948 CH₃ CH₃ CH₃ CF₃ C.949 CH₃ CH₃ C₂H₅ CF₃ C.950 CH₃ CH₃ C₃H₇ CF₃ C.951 CH₃ CH₃ CH(CH₃)₂ CF₃ C.952 CH₃ CH₃ cyclopropyl CF₃ C.953 CH₃ CH₃ CF₃ CF₃ C.954 CH₃ CH₃ OCH₃ CF₃ C.955 CH₃ CH₃ C₆H₅ CF₃ C.956 CH₃ CH₃ 4-F—C₆H₅ CF₃ C.957 CH₃ C₂H₅ H CF₃ C.958 CH₃ C₂H₅ CH₃ CF₃ C.959 CH₃ C₂H₅ C₂H₅ CF₃ C.960 CH₃ C₂H₅ C₃H₇ CF₃ C.961 CH₃ C₂H₅ CH(CH₃)₂ CF₃ C.962 CH₃ C₂H₅ cyclopropyl CF₃ C.963 CH₃ C₂H₅ CF₃ CF₃ C.964 CH₃ C₂H₅ OCH₃ CF₃ C.965 CH₃ C₂H₅ C₆H₅ CF₃ C.966 CH₃ C₂H₅ 4-F—C₆H₅ CF₃ C.967 CH₃ cyclopropyl H CF₃ C.968 CH₃ cyclopropyl CH₃ CF₃ C.969 CH₃ cyclopropyl C₂H₅ CF₃ C.970 CH₃ cyclopropyl C₃H₇ CF₃ C.971 CH₃ cyclopropyl CH(CH₃)₂ CF₃ C.972 CH₃ cyclopropyl cyclopropyl CF₃ C.973 CH₃ cyclopropyl CF₃ CF₃ C.974 CH₃ cyclopropyl OCH₃ CF₃ C.975 CH₃ cyclopropyl C₆H₅ CF₃ C.976 CH₃ cyclopropyl 4-F—C₆H₅ CF₃ C.977 CH₃ CF₃ H CF₃ C.978 CH₃ CF₃ CH₃ CF₃ C.979 CH₃ CF₃ C₂H₅ CF₃ C.980 CH₃ CF₃ C₃H₇ CF₃ C.981 CH₃ CF₃ CH(CH₃)₂ CF₃ C.982 CH₃ CF₃ cyclopropyl CF₃ C.983 CH₃ CF₃ CF₃ CF₃ C.984 CH₃ CF₃ OCH₃ CF₃ C.985 CH₃ CF₃ C₆H₅ CF₃ C.986 CH₃ CF₃ 4-F—C₆H₅ CF₃ C.987 CH₃ Cl H CF₃ C.988 CH₃ Cl CH₃ CF₃ C.989 CH₃ Cl C₂H₅ CF₃ C.990 CH₃ Cl C₃H₇ CF₃ C.991 CH₃ Cl CH(CH₃)₂ CF₃ C.992 CH₃ Cl cyclopropyl CF₃ C.993 CH₃ Cl CF₃ CF₃ C.994 CH₃ Cl OCH₃ CF₃ C.995 CH₃ Cl C₆H₅ CF₃ C.996 CH₃ Cl 4-F—C₆H₅ CF₃ C.997 CH₃ F H CF₃ C.998 CH₃ F CH₃ CF₃ C.999 CH₃ F C₂H₅ CF₃ C.1000 CH₃ F C₃H₇ CF₃ C.1001 CH₃ F CH(CH₃)₂ CF₃ C.1002 CH₃ F cyclopropyl CF₃ C.1003 CH₃ F CF₃ CF₃ C.1004 CH₃ F OCH₃ CF₃ C.1005 CH₃ F C₆H₅ CF₃ C.1006 CH₃ F 4-F—C₆H₅ CF₃ C.1007 CH₃ OCH₃ H CF₃ C.1008 CH₃ OCH₃ CH₃ CF₃ C.1009 CH₃ OCH₃ C₂H₅ CF₃ C.1010 CH₃ OCH₃ C₃H₇ CF₃ C.1011 CH₃ OCH₃ CH(CH₃)₂ CF₃ C.1012 CH₃ OCH₃ cyclopropyl CF₃ C.1013 CH₃ OCH₃ CF₃ CF₃ C.1014 CH₃ OCH₃ OCH₃ CF₃ C.1015 CH₃ OCH₃ C₆H₅ CF₃ C.1016 CH₃ OCH₃ 4-F—C₆H₅ CF₃ C.1017 CH₃ H H CN C.1018 CH₃ H CH₃ CN C.1019 CH₃ H C₂H₅ CN C.1020 CH₃ H C₃H₇ CN C.1021 CH₃ H CH(CH₃)₂ CN C.1022 CH₃ H cyclopropyl CN C.1023 CH₃ H CF₃ CN C.1024 CH₃ H OCH₃ CN C.1025 CH₃ H C₆H₅ CN C.1026 CH₃ H 4-F—C₆H₅ CN C.1027 CH₃ CH₃ H CN C.1028 CH₃ CH₃ CH₃ CN C.1029 CH₃ CH₃ C₂H₅ CN C.1030 CH₃ CH₃ C₃H₇ CN C.1031 CH₃ CH₃ CH(CH₃)₂ CN C.1032 CH₃ CH₃ cyclopropyl CN C.1033 CH₃ CH₃ CF₃ CN C.1034 CH₃ CH₃ OCH₃ CN C.1035 CH₃ CH₃ C₆H₅ CN C.1036 CH₃ CH₃ 4-F—C₆H₅ CN C.1037 CH₃ C₂H₅ H CN C.1038 CH₃ C₂H₅ CH₃ CN C.1039 CH₃ C₂H₅ C₂H₅ CN C.1040 CH₃ C₂H₅ C₃H₇ CN C.1041 CH₃ C₂H₅ CH(CH₃)₂ CN C.1042 CH₃ C₂H₅ cyclopropyl CN C.1043 CH₃ C₂H₅ CF₃ CN C.1044 CH₃ C₂H₅ OCH₃ CN C.1045 CH₃ C₂H₅ C₆H₅ CN C.1046 CH₃ C₂H₅ 4-F—C₆H₅ CN C.1047 CH₃ cyclopropyl H CN C.1048 CH₃ cyclopropyl CH₃ CN C.1049 CH₃ cyclopropyl C₂H₅ CN C.1050 CH₃ cyclopropyl C₃H₇ CN C.1051 CH₃ cyclopropyl CH(CH₃)₂ CN C.1052 CH₃ cyclopropyl cyclopropyl CN C.1053 CH₃ cyclopropyl CF₃ CN C.1054 CH₃ cyclopropyl OCH₃ CN C.1055 CH₃ cyclopropyl C₆H₅ CN C.1056 CH₃ cyclopropyl 4-F—C₆H₅ CN C.1057 CH₃ CF₃ H CN C.1058 CH₃ CF₃ CH₃ CN C.1059 CH₃ CF₃ C₂H₅ CN C.1060 CH₃ CF₃ C₃H₇ CN C.1061 CH₃ CF₃ CH(CH₃)₂ CN C.1062 CH₃ CF₃ cyclopropyl CN C.1063 CH₃ CF₃ CF₃ CN C.1064 CH₃ CF₃ OCH₃ CN C.1065 CH₃ CF₃ C₆H₅ CN C.1066 CH₃ CF₃ 4-F—C₆H₅ CN C.1067 CH₃ Cl H CN C.1068 CH₃ Cl CH₃ CN C.1069 CH₃ Cl C₂H₅ CN C.1070 CH₃ Cl C₃H₇ CN C.1071 CH₃ Cl CH(CH₃)₂ CN C.1072 CH₃ Cl cyclopropyl CN C.1073 CH₃ Cl CF₃ CN C.1074 CH₃ Cl OCH₃ CN C.1075 CH₃ Cl C₆H₅ CN C.1076 CH₃ Cl 4-F—C₆H₅ CN C.1077 CH₃ F H CN C.1078 CH₃ F CH₃ CN C.1079 CH₃ F C₂H₅ CN C.1080 CH₃ F C₃H₇ CN C.1081 CH₃ F CH(CH₃)₂ CN C.1082 CH₃ F cyclopropyl CN C.1083 CH₃ F CF₃ CN C.1084 CH₃ F OCH₃ CN C.1085 CH₃ F C₆H₅ CN C.1086 CH₃ F 4-F—C₆H₅ CN C.1087 CH₃ OCH₃ H CN C.1088 CH₃ OCH₃ CH₃ CN C.1089 CH₃ OCH₃ C₂H₅ CN C.1090 CH₃ OCH₃ C₃H₇ CN C.1091 CH₃ OCH₃ CH(CH₃)₂ CN C.1092 CH₃ OCH₃ cyclopropyl CN C.1093 CH₃ OCH₃ CF₃ CN C.1094 CH₃ OCH₃ OCH₃ CN C.1095 CH₃ OCH₃ C₆H₅ CN C.1096 CH₃ OCH₃ 4-F—C₆H₅ CN C.1097 CH₃ H H Cl C.1098 CH₃ H CH₃ Cl C.1099 CH₃ H C₂H₅ Cl C.1100 CH₃ H C₃H₇ Cl C.1101 CH₃ H CH(CH₃)₂ Cl C.1102 CH₃ H cyclopropyl Cl C.1103 CH₃ H CF₃ Cl C.1104 CH₃ H OCH₃ Cl C.1105 CH₃ H C₆H₅ Cl C.1106 CH₃ H 4-F—C₆H₅ Cl C.1107 CH₃ CH₃ H Cl C.1108 CH₃ CH₃ CH₃ Cl C.1109 CH₃ CH₃ C₂H₅ Cl C.1110 CH₃ CH₃ C₃H₇ Cl C.1111 CH₃ CH₃ CH(CH₃)₂ Cl C.1112 CH₃ CH₃ cyclopropyl Cl C.1113 CH₃ CH₃ CF₃ Cl C.1114 CH₃ CH₃ OCH₃ Cl C.1115 CH₃ CH₃ C₆H₅ Cl C.1116 CH₃ CH₃ 4-F—C₆H₅ Cl C.1117 CH₃ C₂H₅ H Cl C.1118 CH₃ C₂H₅ CH₃ Cl C.1119 CH₃ C₂H₅ C₂H₅ Cl C.2239 CH₃ C₂H₅ C₃H₇ Cl C.2240 CH₃ C₂H₅ CH(CH₃)₂ Cl C.2241 CH₃ C₂H₅ cyclopropyl Cl C.2242 CH₃ C₂H₅ CF₃ Cl C.2243 CH₃ C₂H₅ OCH₃ Cl C.2244 CH₃ C₂H₅ C₆H₅ Cl C.2245 CH₃ C₂H₅ 4-F—C₆H₅ Cl C.2246 CH₃ cyclopropyl H Cl C.2247 CH₃ cyclopropyl CH₃ Cl C.2248 CH₃ cyclopropyl C₂H₅ Cl C.2249 CH₃ cyclopropyl C₃H₇ Cl C.2250 CH₃ cyclopropyl CH(CH₃)₂ Cl C.2251 CH₃ cyclopropyl cyclopropyl Cl C.2252 CH₃ cyclopropyl CF₃ Cl C.2253 CH₃ cyclopropyl OCH₃ Cl C.2254 CH₃ cyclopropyl C₆H₅ Cl C.2255 CH₃ cyclopropyl 4-F—C₆H₅ Cl C.2256 CH₃ CF₃ H Cl C.2257 CH₃ CF₃ CH₃ Cl C.2258 CH₃ CF₃ C₂H₅ Cl C.2259 CH₃ CF₃ C₃H₇ Cl C.2260 CH₃ CF₃ CH(CH₃)₂ Cl C.2261 CH₃ CF₃ cyclopropyl Cl C.2262 CH₃ CF₃ CF₃ Cl C.2263 CH₃ CF₃ OCH₃ Cl C.2264 CH₃ CF₃ C₆H₅ Cl C.2265 CH₃ CF₃ 4-F—C₆H₅ Cl C.2266 CH₃ Cl H Cl C.2267 CH₃ Cl CH₃ Cl C.2268 CH₃ Cl C₂H₅ Cl C.2269 CH₃ Cl C₃H₇ Cl C.2270 CH₃ Cl CH(CH₃)₂ Cl C.2271 CH₃ Cl cyclopropyl Cl C.2272 CH₃ Cl CF₃ Cl C.2273 CH₃ Cl OCH₃ Cl C.2274 CH₃ Cl C₆H₅ Cl C.2275 CH₃ Cl 4-F—C₆H₅ Cl C.2276 CH₃ F H Cl C.2277 CH₃ F CH₃ Cl C.2278 CH₃ F C₂H₅ Cl C.2279 CH₃ F C₃H₇ Cl C.2280 CH₃ F CH(CH₃)₂ Cl C.2281 CH₃ F cyclopropyl Cl C.2282 CH₃ F CF₃ Cl C.2283 CH₃ F OCH₃ Cl C.2284 CH₃ F C₆H₅ Cl C.2285 CH₃ F 4-F—C₆H₅ Cl C.2286 CH₃ OCH₃ H Cl C.2287 CH₃ OCH₃ CH₃ Cl C.2288 CH₃ OCH₃ C₂H₅ Cl C.2289 CH₃ OCH₃ C₃H₇ Cl C.2290 CH₃ OCH₃ CH(CH₃)₂ Cl C.2291 CH₃ OCH₃ cyclopropyl Cl C.2292 CH₃ OCH₃ CF₃ Cl C.2293 CH₃ OCH₃ OCH₃ Cl C.2294 CH₃ CCH₃ C₆H₅ Cl C.2295 CH₃ OCH₃ 4-F—C₆H₅ Cl C.2296 CH₃ CH₃ CH₂CH₂ C.2297 CH₃ CF₃ CH₂CH₂ C.2298 CF₃ CH₃ CH₂CH₂ C.2299 CH₃ C₂H₅ CH₂CH₂ C.2300 C₂H₅ CH₃ CH₂CH₂ C.2301 Cl CH₃ CH₂CH₂ C.2302 CH₃ Cl CH₂CH₂ C.2303 CH₃ CH₃ CH₂CH₂CH₂ C.2304 CH₃ CF₃ CH₂CH₂CH₂ C.2305 CF₃ CH₃ CH₂CH₂CH₂ C.2306 CH₃ C₂H₅ CH₂CH₂CH₂ C.2307 C₂H₅ CH₃ CH₂CH₂CH₂ C.2308 Cl CH₃ CH₂CH₂CH₂ C.2309 CH₃ Cl CH₂CH₂CH₂ C.2310 CH₃ CH₃ CH₂CH₂CH₂CH₂ C.2311 CH₃ CF₃ CH₂CH₂CH₂CH₂ C.2312 CF₃ CH₃ CH₂CH₂CH₂CH₂ C.2313 CH₃ C₂H₅ CH₂CH₂CH₂CH₂ C.2314 C₂H₅ CH₃ CH₂CH₂CH₂CH₂ C.2315 Cl CH₃ CH₂CH₂CH₂CH₂ C.2316 CH₃ Cl CH₂CH₂CH₂CH₂ C.2317 CH₂CH₃ CH₃ H H C.2318 CH₂CH₃ CH₃ CH₃ H C.2319 CH₂CH₃ CH₃ C₂H₅ H C.2320 CH₂CH₃ CH₃ C₃H₇ H C.2321 CH₂CH₃ CH₃ C₄H₉ H C.2322 CH₂CH₃ CH₃ CH(CH₃)₂ H C.2323 CH₂CH₃ CH₃ cyclopropyl H C.2324 CH₂CH₃ CH₃ CF₃ H C.2325 CH₂CH₃ CH₃ OCH₃ H C.2326 CH₂CH₃ CH₃ OC₂H₅ H C.2327 CH₂CH₃ CH₃ CH₂—C₆H₅ H C.2328 CH₂CH₃ CH₃ CH(CH₃)C₆H₅ H C.2329 CH₂CH₃ CH₃ C₆H₅ H C.2330 CH₂CH₃ CH₃ 4-F—C₆H₅ H C.2331 CH₂CH₃ CH₃ 4-Cl-2-pyridyl H C.2332 CH₂CH₃ CH₃ F H C.2333 CH₂CH₃ CH₃ CN H C.2334 CH₂CH₃ C₂H₅ H H C.2335 CH₂CH₃ C₂H₅ CH₃ H C.2336 CH₂CH₃ C₂H₅ C₂H₅ H C.2337 CH₂CH₃ C₂H₅ C₃H₇ H C.2338 CH₂CH₃ C₂H₅ C₄H₉ H C.2339 CH₂CH₃ C₂H₅ CH(CH₃)₂ H C.2340 CH₂CH₃ C₂H₅ cyclopropyl H C.2341 CH₂CH₃ C₂H₅ CF₃ H C.2342 CH₂CH₃ C₂H₅ OCH₃ H C.2343 CH₂CH₃ C₂H₅ OC₂H₅ H C.2344 CH₂CH₃ C₂H₅ CH₂—C₆H₅ H C.2345 CH₂CH₃ C₂H₅ CH(CH₃)C₆H₅ H C.2346 CH₂CH₃ C₂H₅ C₆H₅ H C.2347 CH₂CH₃ C₂H₅ 4-F—C₆H₅ H C.2348 CH₂CH₃ C₂H₅ 4-Cl-2-pyridyl H C.2349 CH₂CH₃ C₂H₅ F H C.2350 CH₂CH₃ C₂H₅ CN H C.2351 CH₂CH₃ CF₃ H H C.2352 CH₂CH₃ CF₃ CH₃ H C.2353 CH₂CH₃ CF₃ C₂H₅ H C.2354 CH₂CH₃ CF₃ C₃H₇ H C.2355 CH₂CH₃ CF₃ C₄H₉ H C.2356 CH₂CH₃ CF₃ CH(CH₃)₂ H C.2357 CH₂CH₃ CF₃ cyclopropyl H C.2358 CH₂CH₃ CF₃ CF₃ H C.2359 CH₂CH₃ CF₃ OCH₃ H C.2360 CH₂CH₃ CF₃ OC₂H₅ H C.2361 CH₂CH₃ CF₃ CH₂—C₆H₅ H C.2362 CH₂CH₃ CF₃ CH(CH₃)C₆H₅ H C.2363 CH₂CH₃ CF₃ C₆H₅ H C.2364 CH₂CH₃ CF₃ 4-F—C₆H₅ H C.2365 CH₂CH₃ CF₃ 4-Cl-2-pyridyl H C.2366 CH₂CH₃ CF₃ F H C.2367 CH₂CH₃ CF₃ CN H C.2368 CH₂CH₃ Cl H H C.2369 CH₂CH₃ Cl CH₃ H C.2370 CH₂CH₃ Cl C₂H₅ H C.2371 CH₂CH₃ Cl C₃H₇ H C.2372 CH₂CH₃ Cl C₄H₉ H C.2373 CH₂CH₃ Cl CH(CH₃)₂ H C.2374 CH₂CH₃ Cl cyclopropyl H C.2375 CH₂CH₃ Cl CF₃ H C.2376 CH₂CH₃ Cl OCH₃ H C.2377 CH₂CH₃ Cl OC₂H₅ H C.2378 CH₂CH₃ Cl CH₂—C₆H₅ H C.2379 CH₂CH₃ Cl CH(CH₃)C₆H₅ H C.2380 CH₂CH₃ Cl C₆H₅ H C.2381 CH₂CH₃ Cl 4-F—C₆H₅ H C.2382 CH₂CH₃ Cl 4-Cl-2-pyridyl H C.2383 CH₂CH₃ Cl F H C.2384 CH₂CH₃ Cl CN H C.2385 CH₂CH₃ OCH₃ H H C.2386 CH₂CH₃ OCH₃ CH₃ H C.2387 CH₂CH₃ OCH₃ C₂H₅ H C.2388 CH₂CH₃ OCH₃ C₃H₇ H C.2389 CH₂CH₃ OCH₃ C₄H₉ H C.2390 CH₂CH₃ OCH₃ CH(CH₃)₂ H C.2391 CH₂CH₃ OCH₃ cyclopropyl H C.2392 CH₂CH₃ OCH₃ CF₃ H C.2393 CH₂CH₃ OCH₃ OCH₃ H C.2394 CH₂CH₃ OCH₃ OC₂H₅ H C.2395 CH₂CH₃ OCH₃ CH₂—C₆H₅ H C.2396 CH₂CH₃ OCH₃ CH(CH₃)C₆H₅ H C.2397 CH₂CH₃ OCH₃ C₆H₅ H C.2398 CH₂CH₃ OCH₃ 4-F—C₆H₅ H C.2399 CH₂CH₃ OCH₃ 4-Cl-2-pyridyl H C.2400 CH₂CH₃ OCH₃ F H C.2401 CH₂CH₃ OCH₃ CN H C.2402 CH₂CH₃ CH₃ H CH₃ C.2403 CH₂CH₃ CH₃ CH₃ CH₃ C.2404 CH₂CH₃ CH₃ C₂H₅ CH₃ C.2405 CH₂CH₃ CH₃ C₃H₇ CH₃ C.2406 CH₂CH₃ CH₃ C₄H₉ CH₃ C.2407 CH₂CH₃ CH₃ CH(CH₃)₂ CH₃ C.2408 CH₂CH₃ CH₃ cyclopropyl CH₃ C.2409 CH₂CH₃ CH₃ CF₃ CH₃ C.2410 CH₂CH₃ CH₃ OCH₃ CH₃ C.2411 CH₂CH₃ CH₃ OC₂H₅ CH₃ C.2412 CH₂CH₃ CH₃ CH₂—C₆H₅ CH₃ C.2413 CH₂CH₃ CH₃ CH(CH₃)C₆H₅ CH₃ C.2414 CH₂CH₃ CH₃ C₆H₅ CH₃ C.2415 CH₂CH₃ CH₃ 4-F—C₆H₅ CH₃ C.2416 CH₂CH₃ CH₃ 4-Cl-2-pyridyl CH₃ C.2417 CH₂CH₃ CH₃ F CH₃ C.2418 CH₂CH₃ CH₃ CN CH₃ C.2419 CH₂CH₃ C₂H₅ H CH₃ C.2420 CH₂CH₃ C₂H₅ CH₃ CH₃ C.2421 CH₂CH₃ C₂H₅ C₂H₅ CH₃ C.2422 CH₂CH₃ C₂H₅ C₃H₇ CH₃ C.2423 CH₂CH₃ C₂H₅ C₄H₉ CH₃ C.2424 CH₂CH₃ C₂H₅ CH(CH₃)₂ CH₃ C.2425 CH₂CH₃ C₂H₅ cyclopropyl CH₃ C.2426 CH₂CH₃ C₂H₅ CF₃ CH₃ C.2427 CH₂CH₃ C₂H₅ OCH₃ CH₃ C.2428 CH₂CH₃ C₂H₅ OC₂H₅ CH₃ C.2429 CH₂CH₃ C₂H₅ CH₂—C₆H₅ CH₃ C.2430 CH₂CH₃ C₂H₅ CH(CH₃)C₆H₅ CH₃ C.2431 CH₂CH₃ C₂H₅ C₆H₅ CH₃ C.2432 CH₂CH₃ C₂H₅ 4-F-C₆H₅ CH₃ C.2433 CH₂CH₃ C₂H₅ 4-Cl-2-pyridyl CH₃ C.2434 CH₂CH₃ C₂H₅ F CH₃ C.2435 CH₂CH₃ C₂H₅ CN CH₃ C.2436 CH₂CH₃ CF₃ H CH₃ C.2437 CH₂CH₃ CF₃ CH₃ CH₃ C.2438 CH₂CH₃ CF₃ C₂H₅ CH₃ C.2439 CH₂CH₃ CF₃ C₃H₇ CH₃ C.2440 CH₂CH₃ CF₃ C₄H₉ CH₃ C.2441 CH₂CH₃ CF₃ CH(CH₃)₂ CH₃ C.2442 CH₂CH₃ CF₃ cyclopropyl CH₃ C.2443 CH₂CH₃ CF₃ CF₃ CH₃ C.2444 CH₂CH₃ CF₃ OCH₃ CH₃ C.2445 CH₂CH₃ CF₃ OC₂H₅ CH₃ C.2446 CH₂CH₃ CF₃ CH₂—C₆H₅ CH₃ C.2447 CH₂CH₃ CF₃ CH(CH₃)C₆H₅ CH₃ C.2448 CH₂CH₃ CF₃ C₆H₅ CH₃ C.2449 CH₂CH₃ CF₃ 4-F—C₆H₅ CH₃ C.2450 CH₂CH₃ CF₃ 4-Cl-2-pyridyl CH₃ C.2451 CH₂CH₃ CF₃ F CH₃ C.2452 CH₂CH₃ CF₃ CN CH₃ C.2453 CH₂CH₃ Cl H CH₃ C.2454 CH₂CH₃ Cl CH₃ CH₃ C.2455 CH₂CH₃ Cl C₂H₅ CH₃ C.2456 CH₂CH₃ Cl C₃H₇ CH₃ C.2457 CH₂CH₃ Cl C₄H₉ CH₃ C.2458 CH₂CH₃ Cl CH(CH₃)₂ CH₃ C.2459 CH₂CH₃ Cl cyclopropyl CH₃ C.2460 CH₂CH₃ Cl CF₃ CH₃ C.2461 CH₂CH₃ Cl OCH₃ CH₃ C.2462 CH₂CH₃ Cl OC₂H₅ CH₃ C.2463 CH₂CH₃ Cl CH₂—C₆H₅ CH₃ C.2464 CH₂CH₃ Cl CH(CH₃)C₆H₅ CH₃ C.2465 CH₂CH₃ Cl C₆H₅ CH₃ C.2466 CH₂CH₃ Cl 4-F—C₆H₅ CH₃ C.2467 CH₂CH₃ Cl 4-Cl-2-pyridyl CH₃ C.2468 CH₂CH₃ Cl F CH₃ C.2469 CH₂CH₃ Cl CN CH₃ C.2470 CH₂CH₃ OCH₃ H CH₃ C.2471 CH₂CH₃ OCH₃ CH₃ CH₃ C.2472 CH₂CH₃ OCH₃ C₂H₅ CH₃ C.2473 CH₂CH₃ OCH₃ C₃H₇ CH₃ C.2474 CH₂CH₃ OCH₃ C₄H₉ CH₃ C.2475 CH₂CH₃ OCH₃ CH(CH₃)₂ CH₃ C.2476 CH₂CH₃ OCH₃ cyclopropyl CH₃ C.2477 CH₂CH₃ OCH₃ CF₃ CH₃ C.2478 CH₂CH₃ OCH₃ OCH₃ CH₃ C.2479 CH₂CH₃ OCH₃ OC₂H₅ CH₃ C.2480 CH₂CH₃ OCH₃ CH₂—C₆H₅ CH₃ C.2481 CH₂CH₃ OCH₃ CH(CH₃)C₆H₅ CH₃ C.2482 CH₂CH₃ OCH₃ C₆H₅ CH₃ C.2483 CH₂CH₃ OCH₃ 4-F—C₆H₅ CH₃ C.2484 CH₂CH₃ OCH₃ 4-Cl-2-pyridyl CH₃ C.2485 CH₂CH₃ OCH₃ F CH₃ C.2486 CH₂CH₃ OCH₃ CN CH₃

The compounds I are suitable as fungicides.

The compounds I are distinguished by outstanding efficacy against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically and can be employed as foliar- and soil-acting fungicides.

They are especially important for controlling a large number of fungi on a variety of crop plants such as wheat, rye, barley, oats, rice, maize, grass, bananas, cotton, soybeans, coffee, sugar cane, grapevines, fruit species, ornamentals and vegetables such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants.

Specifically, they are suitable for controlling the following plant diseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Uncinula necator on grapevines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamentals and grapevines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on a variety of plants, Plasmopara viticola on grapevines, Pseudocercosporella species in hops and cucumbers, Alternaria species on vegetables and fruit and Mycosphaerella species in bananas.

Moreover, the compounds I are suitable for controlling harmful fungi in the protection of materials (eg. wood, paper, paint dispersions, fibers or tissues) and in the protection of stored products.

The compounds I are applied by treating the fungi, or the plants, seeds, materials or the soil to be protected against fungal infection, with a fungicidally active amount of the active ingredients. Application is effected before or after infection of the materials, plants or seeds by the fungi.

They can be converted into the customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the specific intended use; in any case, it should guarantee fine and uniform distribution of the compound according to the invention. The formulations are prepared in a known manner, eg. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent. Suitable auxiliaries are essentially: solvents such as aromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg. methanol, butanol), ketones (eg. cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (eg. kaolins, clays, talc, chalk) and ground synthetic minerals (eg. highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates), and dispersants such as lignin-sulfite waste liquors and methylcellulose.

The fungicidal compositions generally comprise from 0.1 to 95, preferably from 0.5 to 90, % by weight of active ingredient.

Depending on the nature of the desired effect, the rates of application in crop protection are from 0.01 to 2.0 kg of active ingredient per ha.

In the treatment of seed, amounts of active ingredient of from 0.001 to 0.1 g, preferably 0.01 to 0.05 g, are generally required per kilogram of seed.

When used in the protection of materials or stored products, the rate of application of active ingredient depends on the nature of the field of application and on the desired effect. Normal rates of application in the protection of materials are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per cubic meter of material treated.

In the use form as fungicides, the compositions according to the invention can also exist together with other active ingredients, eg. with herbicides, insecticides, growth regulators, fungicides, or else with fertilizers.

A mixture with fungicides frequently results in a widened fungicidal spectrum of action.

The following list of fungicides together with which the compounds according to the invention can be used is intended to illustrate the possible combinations, but not to impose any limitation:

sulfur, dithiocarbamates and their derivatives, such as iron (III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc (N,N′-propylenebisdithiocarbamate), N,N′-polypropylenebis(thiocarbamoyl) disulfide;

nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethyl acrylate, 2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, diisopropyl 5-nitro-isophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-2-triazine, O,O-di-ethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonyl-aminobenzimidazole, 2-(2-furyl)benzimidazole, 2-(4-thiazolyl)-benzimidazole, N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfodiamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thiol oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-di-hydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis(2,2,2-trichloroethyl)formamide, 1-(3,4-di-chloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxy-ethyl)-N′-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, (2RS,3RS)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole, α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene,

strobilurins such as methyl E-methoxyimino-[α-(o-tolyloxy)-o-tolyl]acetate, methyl E-2-{2-[6-[(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, N-methyl-E-methoxyimino-[α-(2-phenoxyphenyl]acetamide, N-methyl-E-methoxyimino-[α-(2,5-dimethylphenoxy)-o-tolyl]acetamide, anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl)-aniline, N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline, N-[4-methyl-6-cyclopropylpyrimidin-2-yl]aniline,

phenylpyrroles such as 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-pyrrole-3-carbonitrile,

cinnamamides such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloylmorpholine,

and a variety of fungicides such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutarimide, hexachlorobenzene, methyl-N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate, DL-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)-alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-amino-butyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl-(5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamide, 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole, 2,4-difluoro-a-(1H-1,2,4-triazolyl-1-methyl)-benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis-(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

The compounds of the formula I are furthermore suitable for effectively controlling pests from the classes of the insects, arachnids and nematodes. They can be employed as pesticides in crop protection and in the hygiene, stored-product and veterinary sector.

The harmful insects include, from the order of the lepidopterans (Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusiani, Zeiraphera canadensis.

From the order of the beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.

From the order of the dipterans (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Tipula paludosa.

From the order of the thrips (Thysanoptera), for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.

From the order of the hymenopterans (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.

From the order of the heteropterans (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.

From the order of the homopterans (Homoptera), for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.

From the order of the termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis.

From the order of the orthopterans (Orthoptera), for example, Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.

From the class of the Arachnoidea, for example, arachnids (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.

From the class of the nematodes, for example, root knot nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stem eelworms and foliar nematodes, eg. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi.

The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of ready-to-spray solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; in any case, they should guarantee the finest possible distribution of the active ingredients according to the invention.

The concentrations of active ingredient in the ready-to-use preparations can be varied within substantial ranges.

In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active ingredients can also be used successfully in the ultra-low-volume method (ULV), it being possible to apply formulations with over 95% by weight of active ingredient, or even the active ingredient without additives.

Under field conditions, the rate of application of active ingredient for controlling pests is 0.1 to 2.0, preferably 0.2 to 1.0, kg/ha.

Substances which are suitable for the preparation of ready-to-spray solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oil and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agent, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active ingredient, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, ligninsulfite waste liquors and methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.

In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

Examples of the formulations are:

I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust which comprises 5% by weight of the active ingredient.

II. 30 parts by weight of a compound according to the invention are mixed intimately with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. This gives a preparation of the active ingredient with good adhesion (comprises 23% by weight of active ingredient).

III. 10 parts by weight of a compound according to the invention are dissolved in a mixture composed of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 9% by weight of active ingredient).

IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenyl and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 16% by weight of active ingredient).

V. 80 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill (comprises 80% by weight of active ingredient).

VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone, which gives a solution which is suitable for use in the form of microdrops (comprises 90% by weight of active ingredient).

VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

VIII. 20 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.

Granules, eg. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients onto solid carriers. Examples of solid carriers are mineral earths such as silicas, silica gels, silicates, talcs, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin such as cereal meal, tree bark meal, wood meal and nut shell meal, cellulose powders, and other solid carriers.

Various types of oils, or herbicides, fungicides, other pesticides, or bactericides, can be added to the active ingredients, if appropriate also only just prior to use (tank mix). These agents can be admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.

SYNTHESIS EXAMPLES

The protocols given in the synthesis examples which follow were used for obtaining further compounds I by altering the starting compounds as required. The resulting compounds are listed in the tables which follow together with physical data.

1. Preparation of methyl methoxyimino-[2-(2-ethoxyimino-1-methyl-propylideneaminooxy)pyridin-3-yl]acetate

1.a 2-Chloro-3-pyridinecarboxylic acid chloride

1131 g (9.5 mol) of thionyl chloride were slowly added dropwise at 90° C. to 500 g (3.17 mol) of 2-chloronicotinic acid. The reaction mixture was stirred for 1 hour at 90° C. and freed from thionyl chloride under reduced pressure (“high vacuum”) at approximately 40° C. This gave 561 g (100%) of the title compound as colorless crystals.

¹H NMR (CDCl₃; δ in ppm): 7.45 (m, 1H, pyridyl); 8.42 (dd, 1H, pyridyl); 8.62 (dd, 1H, pyridyl);

IR: 3060, 1786, 1570, 1556, 1392, 1261, 1188, 865, 816, 746, 726 cm⁻¹.

1.b 2-(2-Chloropyridin-3-yl)glyoxylic acid cyanide

A mixture of 558 g (3.18 mol) of 2-chloro-3-pyridinecarboxylic acid chloride, 566 g (6.23 mol) of copper(I) cyanide and 4000 ml of acetonitrile was stirred for 1 hour at room temperature and then refluxed for 2 hours. The reaction mixture was freed from solvent under reduced pressure (“high vacuum”) at approximately 40° C. and the residue was boiled up twice with approximately 1 l of toluene and filtered off. The combined organic phases were freed from solvent under reduced pressure (“high vacuum”) at approximately 40° C. This gave 348 g (62%) of the title compound as brown crystals.

IR: 2220, 1730, 1574, 1559, 1399, 1259, 1066, 871, 746, 728 cm⁻¹.

1.c Methyl 2-(2-chloropyridin-3-yl)glyoxylate

A mixture of 83 g (0.47 mol) of 2-(2-chloropyridin-3-yl)glyoxylic acid cyanide and 500 ml of concentrated HCl was stirred for 8 hours at 50° C. The reaction solution was concentrated at approximately 40° C. under reduced pressure (“high vacuum”), treated twice with 100 ml of toluene, and the solvent was removed at approximately 40° C. under reduced pressure (“high vacuum”). The residue was dissolved in 500 ml of methanol and 5 ml of concentrated H₂SO₄ and refluxed for 20 hours. The solvent was removed at approximately 40° C. under reduced pressure (“high vacuum”), and the residue was taken up in 500 ml of ethyl acetate and washed with saturated sodium hydrogen carbonate solution. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was subjected to fractional distillation over a packed column 20 cm in length. This gave 18.3 g (19%) of the title compound as a yellow oil of boiling point 105-115° C. at 0.2-0.3 mbar.

¹H NMR (CDCl₃; δ in ppm): 4.0 (s, 3H, OCH₃); 7.45 (m, 1H, pyridyl); 8.1 (dd, 1H, pyridyl); 8.6 (dd, 1H, pyridyl);

MS m/z (intensity): 199 (M⁺, 8), 186 (20), 142 (50), 140 (100), 114 (18), 112 (40), 76 (24), 50 (10), 18 (16).

1. d Methyl [2-(2-ethoxyimino-1-methyl-propylideneaminooxy)pyridin-3-yl]glyoxylate

A mixture of 3.25 g (22.6 mmol) of 2-ethoxyimino-3-hydroxyiminobutane and 25 ml of tert-butanol was treated with 2.53 g (22.6 mmol) of potassium tert-butoxide at 60° C. and stirred for 1 hour at the same temperature. The reaction mixture was freed from solvent under reduced pressure (“high vacuum”) at approximately 40° C. The residue was introduced into 15 ml of dimethyl sulfoxide, and 4.5 g (22.6 mmol) of methyl 2-(2-chloropyridin-3-yl)glyoxylate, dissolved in 5 ml of dimethyl sulfoxide, were added at 50° C. The mixture was stirred for 20 hours at room temperature, and the reaction mixture was poured onto approximately 150 g of ice and extracted repeatedly with ethyl acetate. The organic phases were combined, washed with water and dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography over silica gel using cyclohexane/ethyl acetate (4/1) as the eluent. This gave 1.56 g (23%) of the title compound as a white solid.

¹H NMR (CDCl₃; δ in ppm): 1,3 (t, 3H, CH₃); 2.04 (s, 3H, CH₃); 2.3 (s, 3H, CH₃); 3.82 (s, 3H, OCH₃); 4.28 (q, 2H, OCH₂); 7.22 (m, 1H, pyridyl); 8.1 (dd, 1H, pyridyl); 8.5 (dd, 1H, pyridyl);

M.P.: 75° C.

1.e Methyl methoxyimino-[2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]-glyoxylate

A mixture of 800 mg (2.6 mmol) of methyl [2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]-glyoxylate and 410 mg of pyridine in 10 ml of methanol was treated with 240 mg (2.9 mmol) of O-methylhydroxylamine hydrochloride and heated for 1 hour to 50° C. The reaction mixture was freed from solvent under reduced pressure, and the residue was taken up in ethyl acetate and washed with dilute aqueous NaCl solution. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography over silica gel using cyclohexane/ethyl acetate (4/1) as the eluent. This gave 480 mg (55%) of the title compound as a white solid.

¹H NMR (CDCl₃; δ in ppm): 1.3 (t, 3H, CH₃); 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 3.82 (s, 3H, OCH₃); 4.06 (s, 3H, OCH₃); 4.12 (q, 2H, OCH₂); 7.1 (m, 1H, pyridyl); 7.7 (dd, 1H, pyridyl); 8.38 (dd, 1H, pyridyl);

M.p.: 71° C.

150 mg (17%) of methyl Z-methoxyimino-[2-E,E-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]glyoxylate were isolated as a second product in the form of a yellow oil.

¹H NMR (CDCl₃; δ in ppm): 1.3 (t, 3H, CH₃); 2.18 (s, 3H, CH₃); 2.24 (s, 3H, CH₃); 3.8 (s, 3H, OCH₃); 4.06 (s, 3H, OCH₃); 4.12 (q, 2H, OCH₂); 7.14 (m, 1H, pyridyl); 8.0 (dd, 1H, pyridyl); 8.4 (dd, 1H, pyridyl);

IR: 2980, 2940, 1752, 1587, 1418, 1252, 1227, 1209, 1048, 1027, 913, 893 cm⁻¹.

2. Preparation of N-methyl-methoxyimino-[2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]acetamide

A mixture of 260 mg (0.77 mmol) of methyl oxyimino-[2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]glyoxylate and 2 g of 40% strength aqueous methylamine solution in 3 ml of tetrahydrofuran was refluxed for 2 hours. The reaction mixture was freed from solvent under reduced pressure; the residue was taken up in ethyl acetate; and the mixture was washed with dilute aqueous NaCl solution. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. This gave 240 mg (93%) of the title compound as a white solid.

¹H NMR (CDCl₃; δ in ppm): 1.3 (t, 3H, CH₃); 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 2.90, 2.92 (in each case s, 3H, NCH₃); 3.95 (s, 3H, OCH₃); 4.25 (q, 2H, OCH₂); 6.8 (m, 1H, NH); 7.1 (m, 1H, pyridyl); 7.65 (dd, 1H, pyridyl); 8.35 (dd, 1H, pyridyl);

M.p.: 110° C.

3. Preparation of methyl methoxyimino-[2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]acrylate

A mixture of 650 mg (1.9 mmol) of methoxymethyltriphenyl-phosphonium chloride and 340 g (1.9 mmol) of sodium methoxide solution (30% strength in methanol) in 8 ml of dimethylformamide was stirred for 10 minutes at room temperature. The reaction mixture was subsequently treated with 400 mg (0.95 mmol) of methyl [2-(2-ethoxyimino-1-methylpropylideneaminooxy)pyridin-3-yl]glyoxylate, dissolved in 4 ml of dimethylformamide. The reaction mixture was stirred for 4 hours at room temperature, hydrolyzed with 20 ml of water, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. This gave 120 mg (38%) of the title compound as a yellow oil.

¹H NMR (CDCl₃; δ in ppm): 1.3 (t, 3H, CH₃); 2.16 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 3.7 (s, 3H, OCH₃); 3.84 (s, 3H, OCH₃); 4.22 (q, 2H, OCH₂); 7.1 (m, 1H, pyridyl); 7.58 (s, 1H, CH); 7.6 (dd, 1H, pyridyl); 8.25 (dd, 1H, pyridyl);

IR: 2950, 2920, 2850, 1713, 1435, 1416, 1291, 1263, 1238, 1132, 1105, 1050, 914 cm⁻¹.

TABLE

(1.8) No. R R¹ R³ Y¹ R⁴ ¹H NMR [δ in ppm; CDCl₃] 1 Ic CH₃ CH₃ O CH₃ 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 3.82 (s, 3H, OCH₃); 4.0 (s, 3H, OCH₃); 4.05 (s, 3H, OCH₃); 7.15 (m, 1H, Py); 7.7 (dd, 1H, Py); 8.35 (dd, 1H, Py) 2 Ic CH₃ CH₃ O CH(CH₃)₂ 1.3 (d, 6H, 2XCH₃); 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 3.84 (s, 3H, OCH₃); 4.06 (s, 3H, OCH₃); 4.45 (m, 1H, CH); 7.14 (m, 1H, Py); 7.7 (dd, 1H, Py); 8.38 (dd, 1H, Py) 3 Ic CH₃ CH₃ O CH₂C═CH 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 2.5 (s, 1H, CH); 3.82 (s, 3H, OCH₃); 4.05 (s, 3H, OCH₃); 4.8 (s, 2H, OCH₂); 7.1 (m, 1H, Py); 7.7 (dd, 1H, Py); 8.38 (dd, 1H, Py) 4 Ic CH₃ CH₃ O CH₂—C₆H₅ 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 3.8 (s, 3H, OCH₃); 4.05 (s, 3H, OCH₃); 5.2 (s, 2H, OCH₂); 7.1 (m, 1H, Py); 7.32 (m, 5H, benzyl); 7.7 (dd, 1H, Py); 8.35 (dd, 1H, Py) 5 Id CH₃ CH₃ O CH₃ 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 2.89; 2.90 (in each case s, 3H, NCH₃); 3.95 (s, 3H, OCH₃); 4.0 (s, 3H, OCH₃); 6.95 (m, 1H, NH); 7.1 (m, 1H, Py); 7.65 (dd, 1H, Py); 8.3 (dd, 1H, Py) 6 Id CH₃ CH₃ O CH(CH₃)₂ 1.35 (d, 6H, 2xCH₃); 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 2.90; 2.92 (in each case s, 3H, NCH₃); 3.95 (s, 3H, OCH₃); 4.4 (m, 1H, CH); 6.85 (m, 1H, NH); 7.1 (m, 1H, Py); 7.65 (dd, 1H, Py); 8.35 (dd, 1H, Py) 7 Id CH₃ CH₃ O CH₂C≡CH 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 2.5 (s, 1H, CH); 2.90; 2.92 (in each case s, 3H, NCH₃); 3.95 (s, 3H, OCH₃); 2.5 (s, 1H, CH); 4.8 (s, 2H, OCH₂); 6.75 (m, 1H, NH); 7.1 (m, 1H, Py); 7.7 (dd, 1H, Py); 8.35 (dd, 1H, Py) 8 Id CH₃ CH₃ O CH₂—C₆H₅ 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 2.90; 2.92 (in each case s, 3H, NCH₃); 3.95 (s, 3H, OCH₃); 5.22 (s, 2H, OCH₂); 6.75 (m, 1H, NH); 7.1 (m, 1H, Py); 7.38 (m, 5H, benzyl); 7.64 (dd, 1H, Py); 8.36 (dd, 1H, Py) 9 Ic CH₂CH₃ CH₃ O CH₃ 1.1 (t, 3H, CH₃); 2.1 (s, 3H, CH₃); 2.75 (q, 2H, CH₂); 3.84 (s, 3H, OCH₃); 4.0 (s, 3H, OCH₃); 4.06 (s, 3H, OCH₃); 7.12 (m, 1H, Py); 7.65 (dd, 1H, Py); 8.38 (dd, 1H, Py) 10 Ic CH₂CH₃ CH₃ O CH(CH₃)₂ 1.12 (t, 3H, CH₃); 1.3 (d, 6H, 2xCH₃); 2.05 (s, 3H, CH₃); 2.75 (q, 2H, CH₂); 3.82 (s, 3H, OCH₃); 4.06 (s, 3H, OCH₃); 4.45 (m, 1H, CH); 7.1 (m, 1H, Py); 7.65 (dd, 1H, Py); 8.36 (dd, 1H, Py) 11 Ic CH₂CH₃ CH₃ O CH₂C≡CH 1.1 (t, 3H, CH₃); 2.1 (s, 3H, CH₃); 2.5 (s, 1H, CH); 2.75 (q, 2H, CH₂); 3.86 (s, 3H, OCH₃); 4.06 (s, 3H, OCH₃); 4.8 (s, 2H, OCH₂); 7.14 (m, 1H, Py); 7.65 (dd, 1H, Py); 8.38 (dd, 1H, Py) 12 Id CH₂CH₃ CH₃ O CH₃ 1.1 (t, 3H, CH₃); 2.06 (s, 3H, CH₃); 2.75 (q, 2H, CH₂); 2.90; 2.92 (in each case s, 3H, NCH₃); 3.94 (s, 3H, OCH₃); 4.0 (s, 3H, OCH₃); 6.8 (m, 1H, NH); 7.1 (m, 1H, Py); 7.65 (dd, 1H, Py); 8.36 (dd, 1H, Py) 13 Id CH₂CH₃ CH₃ O CH(CH₃)₂ 1.1 (t, 3H, CH₃); 1.25 (d, 6H, 2xCH₃); 2.05 (s, 3H, CH₃); 2.75 (q, 2H, CH₂); 2.90; 2.92 (in each case s, 3H, NCH₃); 3.94 (s, 3H, OCH₃) 4.42 (m, 1H, CH); 6.8 (m, 1H, NH); 7.1 (m, 1H, Py); 7.65 (dd, 1H, Py); 8.36 (dd, 1H, Py) 14 Id CH₂CH₃ CH₃ O CH₂C≡CH 1.12 (t, 3H, CH₃); 2.1 (s, 3H, CH₃); 2.5 (s, 1H, CH); 2.75 (q, 2H, CH₂); 2.90; 2.92 (in each case s, 3H, NCH₃); 3.96 (s, 3H, OCH₃); 4.8 (s, 2H, OCH₂); 6.8 (m, 1H, NH); 7.12 (m, 1H, Py); 7.65 (dd, 1H, Py); 8.35 (dd, 1H, Py) 15 Ic CH₃ CH₃ O CH₂CH₃ 1.3 (t, 3H, CH₃); 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 3.82 (s, 3H, OCH₃); 4.06 (s, 3H, OCH₃); 4.12 (q, 2H, OCH₂); 7.1 (m, 1H, Py); 7.7 (dd, 1H, Py); 8.38 (dd, 1H, Py) 16 Id CH₃ CH₃ O CH₂CH₃ 1.3 (t, 3H, CH₃); 2.1 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 2.90; 2.92 (in each case s, 3H, NCH₃); 3.95 (s, 3H, OCH₃); 4.25 (q, 2H, OCH₂); 6.8 (m, 1H, NH); 7.1 (m, 1H, Py); 7.65 (dd, 1H, Py); 8.35 (dd, 1H, Py) 17 Ia CH₃ CH₃ O CH₂CH₃ 1.3 (t, 3H, CH₃); 2.16 (s, 3H, CH₃); 2.2 (s, 3H, CH₃); 3.7 (s, 3H, OCH₃); 3.84 (s, 3H, OCH₃); 4.22 (q, 2H, OCH₂); 7.1 (m, 1H, Py); 7.58 (s, 1H, CH); 7.6 (dd, 1H, Py); 8.25 (dd, 1H, Py) 18 Ic CH₂CH₃ CH₃ O CH₂CH₃ 1.1 (t, 3H, CH₃); 1.3 (t, 3H, CH₃); 2.1 (s, 3H, CH₃); 2.75 (q, 2H, CH₂); 3.85 (s, 3H, OCH₃); 4.06 (s, 3H, OCH₃); 4.24 (q, 2H, OCH₂); 7.1 (m, 1H, Py); 7.68 (dd, 1H, Py); 8.38 (dd, 1H, Py) 19 Ia CH₂CH₃ CH₃ O CH(CH₃)₂ 1.1 (t, 3H, CH₃); 1.15 (d, 6H, 2xCH₃); 2.1 (s, 3H, CH₃); 2.74 (q, 2H, CH₂); 3.7 (s, 3H, OCH₃); 3.84 (s, 3H, OCH₃); 4.42 (m, 1H, CH); 7.1 (m, 1H, Py); 7.58 (m, 2H, 1xCH, 1xPy); 8.3 (dd, 1H, Py)

Ia=C[CO₂CH₃]=CHOCH₃; Ib=C[CO₂CH₃]=CHCH₃;

Ic=C[CO₂CH₃]=NOCH₃; Id=C[CONHCH₃]=NOCH₃

Py=pyridyl

Examples of the Action Against Harmful Fungi

The fungicidal function of the compounds of the general formula I was demonstrated by the following experiments:

The active ingredients were formulated, separately or jointly, as a 10% emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Wettol® EM (nonionic emulsifier based on ethoxylated castor oil) and diluted with water to give the desired concentration.

Activity Against Erysiphe graminis var. tritici (powdery mildew of wheat)

Leaves of wheat seedlings (cultivar: “Frühgold”) were first treated with the aqueous preparation of the active ingredients (rate of application: 250 ppm). After approximately 24 hours, the plants were dusted with spores of powdery mildew of wheat (Erysiphe graminis var. tritici). The treated plants were subsequently incubated for 7 days at 20-22° C. and a relative atmospheric humidity of 75-80%. The extent of fungal development was subsequently determined.

In this test, the infection level of plants which had been treated with the compounds 1, 3 and 7 according to the invention was 15% and less, while the infection level of the untreated (control) plants was 75%.

Activity Against Plasmopara viticola (downy mildew grapevines)

Grapevines in pots (cultivar: “Müller Thurgau”) were sprayed to run off with the preparation of active ingredient (rate of application: 250 ppm). After 8 days, the plants were sprayed with a zoospore suspension of the fungus Plasmopara viticola and kept for 5 days at 20-30° C. and high atmospheric humidity. Thereupon, prior to assessment, the plants were kept for 16 hours at high atmospheric humidity. The test was evaluated visually.

In this test, the infection level of the plants which had been treated with the compounds 1, 3 and 7 according to the invention was 15% and less, while the infection level of the untreated (control) plants was 70%.

Examples of the Action Against Animal Pests

The activity of the compounds of the general formula I against animal pests was demonstrated by the following experiments:

The active ingredients were formulated

a. as a 0.1% strength solution in acetone or

b. as a 10% emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Wettol® EM (non-ionic emulsifier based on ethoxylated castor oil)

and diluted to give the desired concentration, using acetone in the case of a. and water in the case of b.

After the experiments had been concluded, in each case the lowest concentration at which the compounds still caused an 80 to 100% inhibition, or mortality, in comparison with untreated controls was determined (limit or minimal concentration). 

We claim:
 1. A pyridine compound of the formula I

wherein: X is cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and C₃-C₆-cycloalkyl; n is 0, 1, 2 or 3, it being possible for the substituents X to be different when n is greater than 1; Y is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C₁-C₄-alkyl group; R is C(CO₂CH₃)═CHCH₃, C(CO₂CH₃)═CHOCH₃, C(CO₂CH₃)═NOCH₃, C(CONH₂)═NOCH₃ or C(CONHCH₃)═NOCH₃; R¹ is hydrogen, hydroxyl, cyano, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, aryl, aryl-C₁-C₄-alkyl, aryloxy-C₁-C₄-alkyl and aryl-C₁-C₄-alkoxy, it being possible for the aromatic rings to be partially or fully halogenated and/or to have attached to them one to three of the following radicals: cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, and C(CH₃)═N-A¹-R^(a); R^(a) is C₁-C₆-alkyl, A¹ is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C₁-C₄-alkyl group; R² is unsubstituted or substituted alkenyl, or —Q—C(R³)═N-Y¹-R⁴ where Q is a direct bond, CH₂, CH(CH₃), CH(CH₂CH₃) or 1,1-cyclopropyl; Y¹ is oxygen or nitrogen, the nitrogen atom having attached to it a hydrogen atom or a C₁-C₄-alkyl group; R³ is one of the groups listed under R¹, or unsubstituted or substituted cycloalkoxy, heterocyclyloxy, aryloxy, hetaryloxy, arylthio and hetarylthio; R⁴ is unsubstituted or substituted C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₁₀-alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl, C₂-C₁₀-alkynylcarbonyl or C₁-C₁₀-alkylsulfonyl; unsubstituted or substituted aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl; or a salt thereof.
 2. A compound of the formula I as claimed in claim 1 wherein R² is a substituted alkenyl, the substituents being from one to three of the following radicals has the following meanings: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkylcarbonyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyloxy, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, wherein the aromatic ring are substituted or unsubstituted.
 3. A compound of the formula I as claimed in claim 1 where R² is the group —C(R³)═N—Y¹—R⁴ wherein: Y¹ is O, NH or N(CH₃); R⁴ is hydrogen, C₁-C₆-alkyl which optionally has attached to it one of the following groups: C₁-C₄-alkoxy, C₃-C₆-cycloalkyl which is unsubstituted or substituted or phenyl which is unsubstituted or substituted; C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl or C₃-C₆-cycloalkyl which is unsubstituted or substituted by customary groups, R³ is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy or C₃-C₆-cycloalkyl.
 4. A compound of the formula I.8 as claimed in claim 1

wherein: R is C(CO₂CH₃)═CHCH₃, C(CO₂CH₃)═CHOCH₃, C(CO₂CH₃)═NOCH₃ or C(CONHCH₃═NOCH₃; X is cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl; n is 0 or 1; R¹ is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl; R³ is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl; Y¹ is O,NH or N(CH₃); R⁴ is hydrogen, C₁-C₆-alkyl which may have attached to it one of the following groups: C₁-C₄-alkoxy, C₃-C₆-cycloalkyl which is unsubstituted or substituted by customary groups or phenyl which is unsubstituted or substituted; C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkynyl or C₃-C₆-cycloalkyl which is unsubstituted or substituted by customary groups.
 5. A compound of the formula I as claimed in claim 1 where R² is the group —C(R^(x))═CR^(y)R^(z) with the following meanings: R^(x) is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl; R^(y) is hydrogen, C₁-C₆-alkyl which may be partially or fully halogenated and/or may have attached to it one to three (in particular one) of the following groups: C₁-C₄-alkoxy, C₃-C₆-cycloalkyl which is unsubstituted or substituted by customary groups or phenyl which is unsubstituted or substituted; C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl which is unsubstituted or substituted by customary groups; phenyl which is unsubstituted or substituted by customary groups, pyridyl which is unsubstituted or substituted by customary groups or pyrimidyl which is unsubstituted or substituted; R^(z) is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl and C₃-C₆-cycloalkyl, or R^(y) and R^(x) together with the double bond to which they are attached are C₄-C₆-cycloalkenyl.
 6. A compound of the formula I.12 as claimed in claim 1

wherein: R is C(CO₂CH₃)═CHCH₃, C(CO₂CH₃)═CHOCH₃, C(CO₂CH₃)═NOCH₃ or C(CONHCH₃═NOCH₃; X is cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl; n is 0 or 1; R¹ is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl; R^(x) is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy and C₃-C₆-cycloalkyl; R^(y) is hydrogen, C₁-C₆-alkyl which may be partially or fully halogenated and/or may have attached to it one to three (in particular one) of the following groups: C₁-C₄-alkoxy, C₃-C₆-cycloalkyl which is unsubstituted or substituted by customary groups or phenyl which is unsubstituted or substituted; C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl which is unsubstituted or substituted by customary groups; phenyl which is unsubstituted or substituted by customary groups, pyridyl which is unsubstituted or substituted by customary groups or pyrimidyl which is unsubstituted or substituted; R^(z) is hydrogen, cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl and C₃-C₆-cycloalkyl, or R^(y) and R^(x) together with the double bond to which they are attached are C₄-C₆-cycloalkenyl.
 7. A compound as claimed in claim 1 where n is 0 or 1 and, when n is 1, X is fluorine, chlorine, methyl or trifluoromethyl.
 8. A compound as claimed in any of claim 1 where R¹ is C₁-C₃-alkyl.
 9. A compound as claimed in claim 4 where R³ is C₁-C₃-alkyl, Y¹ is oxygen and R⁴ is C₁-C₄-alkyl, C₃-C₄-alkynyl or benzyl.
 10. A compound as claimed in claim 6 where R^(x) is C₁-C₄-alkyl, R^(y) is C₁-C₄-alkyl or phenyl which for its part may have attached to it one to three of the following radicals: halogen, C₁-C₄-alkyl or haloalkyl; and R^(z) is hydrogen.
 11. A compound of the formula I as claimed in claim 1 where the radical R and the group —Y—N═CR¹R² are bonded to two adjacent C atoms of the pyridyl ring.
 12. A process for the preparation of the pyridine compounds of the formula I as claimed in claim 1 where R is C(CO₂CH₃)═CHCH₃, C(CO₂CH₃)═CHOCH₃ or C(CO₂CH₃)═NOCH₃, which comprises first converting a pyridinecarboxylic acid of the formula IIa

where L¹ is a nucleophilically exchangeable leaving group and R# is hydrogen or a C₁-C₄-alkyl group into the acid chloride IIb

and subsequently into the acid cyanide IIc

reacting IIc via a Pinner reaction to give the corresponding α-keto ester IIIa

subsequently reacting IIIa with an oxime of the formula IV

in the presence of a base to give the corresponding α-keto ester IIIb

and subsequently converting IIIb either a) with a Wittig or Wittig-Horner reagent of the formula Va CH₃—O—CH₂—P*  (Va) where P* is a phosphonate or a phosphonium halide radical into the corresponding compound Ia, [R=C(CO₂CH₃)═CHOCH₃, or b) with a Wittig or Wittig-Horner reagent of the formula Vb CH₃—CH₂—P*  (Vb) into the corresponding compound Ib [R=C(CO₂CH₃)═CHCH₃], or c) with O-methylhydroxylamine or a salt thereof (Vc) CH₃—O—NH₂CH₃—O—NH₃ ^(⊖)Z^(⊕)  (Vc) where Z⁻ is a halide anion into the corresponding compound Ic, wherein R is C(CO₂CH₃)═NOCH₃.
 13. A process for the preparation of the compounds Va and Vc as set forth in claim 12, which comprises converting a pyridine compound of the formula VI

where L¹ is a nucleophilically exchangeable leaving group and M is an organometallic radical with a compound VII

where T is CH, CHO or NO and Hal is a halogen atom in the presence of a catalyst into the corresponding pyridine derivative of the formula VIII

and subsequently reacting VIII with an oxime of the formula IV as set forth in claim 12 in the presence of a base to give Ia or Ic.
 14. A process for the preparation of the compounds I as claimed in claims 12 where R is C(CONHCH₃)═NOCH₃, which comprises converting a compound of the formula Ic as set forth in claim 12 with methylamine or a salt thereof (IX) CH₃—NH₂CH₃—NH₃ ^(⊕)Z^(⊖)  (IX) where Z⁻ is a halide anion into the corresponding compound Id, wherein R is C(CONHCH₃) NOCH₃].
 15. A composition which is suitable for controlling animal pests or harmful fungi, comprising a solid or liquid carrier and a compound of the formula I as claimed in claim
 1. 16. A method of controlling harmful fungi, which comprises treating the fungi, or the materials, the plants, the soil or seed to be protected against fungal infection with an effective amount of a compound of the formula I as claimed in claim
 1. 17. A method of controlling animal pests, which comprises treating the pests, or the materials, plants, the soil or seed to be protected against them with an effective amount of a compound of the formula I as claimed in any of claim
 1. 